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«Signature: _ Stephen Wilson Date Synthesis and Reactivity of Benzo[1,3,2]dithiazole 1,1-dioxides: Implications in Acylative Redox Dehydration By ...»

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To a round-bottom flask equipped with a magnetic stir bar was added sulfonyl chloride (1.0 equiv), base (1.1 equiv) and DCM (0.50 M). Amine (1.1 equiv) was then added slowly and the reaction stirred at room temperature until completion as indicated by TLC. Upon completion the reaction was diluted with DCM and washed with saturated sodium bicarbonate. The organic layer was then dried with MgSO4 and concentrated to give product. When necessary, product was purified by recrystallization from appropriate solvent.

2-bromo-N-isopropylbenzenesulfonamide. Following method A, from 2bromobenzenesulfonyl chloride (3.00 g, 11.7 mmol) and isopropylamine (2.9 mL, 35.2 mmol) was obtained clean product after recrystallization from ethanol and water. White solid (3.17 g,

11.4 mmol, 97 % yield); m.p. 102 - 104 oC; 1H NMR (400 MHz, CDCl3) δ 8.14 (dd, J = 7.7, 1.9 Hz, 1H), 7.71 (dd, J = 7.7, 1.3 Hz, 1H), 7.45 (td, J = 7.5, 1.3 Hz, 1H), 7.39 (td, J = 7.5, 1.9 Hz, 1H), 4.99 (d, J = 7.5 Hz, 1H), 3.53 – 3.28 (m, 1H), 1.07 (d, J = 6.5 Hz, 6H); 13C NMR (101 MHz, CDCl3) δ 139.8, 135.0, 133.5, 131.3, 127.8, 119.7, 46.6, 23.4; HRMS (ESI) Calcd for C9H13BrNO2S [M+H+] 277.9845, found 277.9856; IR (neat) 3371 cm-1 2-bromo-N-phenylbenzenesulfonamide. Following method B, from 2-bromobenzenesulfonyl

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was obtained clean product after recrystallization from ethanol. White solid (5.23 g, 16.8 mmol, 82 % yield); m.p. 132 - 134 oC (lit. 137 - 138 oC)30; 1H NMR (400 MHz, CDCl3) δ 8.04 – 7.88 (m, 1H), 7.67 – 7.57 (m, 1H), 7.30 – 7.25 (m, 2H), 7.20 – 6.98 (m, 6H); 13C NMR (100 MHz, CDCl3) δ 137.9, 135.8, 135.1, 134.2, 132.4, 129.5, 127.9, 125.9, 121.8, 119.8; IR (neat) 3281 cm-1 2-bromo-N-(2,6-dimethylphenyl)benzenesulfonamide. Following method B, from 2bromobenzenesulfonyl chloride (5.00 g, 19.6 mmol), pyridine (6.30 mL, 78.0 mmol) and 2,6dimethylaniline (2.41 mL, 19.6 mmol) was obtained clean product without further purification.

Orange solid (6.27 g, 18.4 mmol, 94 % yield); m.p. 159 - 160 oC; 1H NMR (400 MHz, CDCl3) δ 8.06 – 7.88 (m, 1H), 7.82 – 7.74 (m, 1H), 7.46 – 7.36 (m, 2H), 7.08 (dd, J = 8.4, 6.6 Hz, 1H), 7.00 (d, J = 7.1 Hz, 2H), 6.54 (s, 1H), 2.10 (s, 6H); 13C NMR (101 MHz, CDCl3) δ 141.5, 138.4, 135.0, 133.5, 132.5, 130.4, 128.6, 128.3, 127.8, 120.0, 18.8; HRMS (ESI) Calcd for C14H15BrNO2S [M+H+] 340.0001, found 339.9994; IR (neat) 3303 cm-1 2-chloro-N-isopropyl-5-nitrobenzenesulfonamide. Following method A from 2-chloro-5nitrobenzenesulfonyl chloride (3.0 g, 11.7 mmol) and isopropylamine (2.9 mL, 35.1 mmol) was

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m.p. 170 - 172 oC; 1H NMR (400 MHz, CDCl3) δ 8.92 (d, J = 2.7 Hz, 1H), 8.33 (dd, J = 8.7, 2.7 Hz, 1H), 7.72 (d, J = 8.7 Hz, 1H), 5.05 (d, J = 7.9 Hz, 1H), 3.52 (dp, J = 7.9, 6.5 Hz, 1H), 1.11 (d, J = 6.5 Hz, 6H); 13C NMR (101 MHz, CDCl3) δ 146.5, 140.5, 138.3, 133.1, 128.0, 126.3, 47.2, 23.8; HRMS (ESI) Calcd for C9H11ClNaN2O4S [M+Na+] 301.0020, found 301.0022; IR (neat) 3283 cm-1 2-chloro-5-nitro-N-phenylbenzenesulfonamide. Following method B from 2-chloro-5nitrobenzenesulfonyl chloride (3.00 g, 11.7 mmol), pyridine (1.04 mL, 12.9 mmol) and aniline (1.17 mL, 12.9 mmol) was obtained clean product after recrystallization from ethanol and water.

Yellow solid (2.95 g, 9.4 mmol, 81 % yield); m.p. 168 - 169 oC; 1H NMR (600 MHz, CDCl3) δ 8.80 (dd, J = 2.7, 0.8 Hz, 1H), 8.28 (ddd, J = 8.7, 2.7, 0.8 Hz, 1H), 7.69 (dd, J = 8.7, 0.8 Hz, 1H), 7.30 – 7.17 (m, 2H), 7.16 – 7.06 (m, 4H); 13C NMR (75 MHz, CDCl3) δ 146.4, 138.1, 134.8, 133.0, 129.9, 128.5, 127.2, 126.7, 122.0; HRMS (ESI) Calcd for C12H19ClNaN2O4S [M+Na+] 334.9864, found 334.9868; IR (neat) 3285 cm-1 2-chloro-N-(2,6-dimethylphenyl)-5-nitrobenzenesulfonamide. Following method B, from 2chloro-5-nitrobenzenesulfonyl chloride (1.46 g, 5.7 mmol), pyridine (0.55 mL, 6.8 mmol) and

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ethanol and water. Orange solid (1.29 g, 3.8 mmol, 66 % yield); m.p. 161 - 162 oC; 1H NMR (400 MHz, CDCl3) δ 8.75 (d, J = 2.7 Hz, 1H), 8.34 (dd, J = 8.7, 2.7 Hz, 1H), 7.76 (d, J = 8.7 Hz, 1H), 7.18 – 7.07 (m, 1H), 7.02 (d, J = 7.6 Hz, 2H), 6.58 (s, 1H), 2.10 (s, 6H); 13C NMR (101 MHz, CDCl3) δ 146.2, 141.4, 138.3, 138.2, 132.8, 131.8, 128.9, 128.8, 127.8, 125.3, 18.8;

HRMS (ESI) Calcd for C14H13ClNaN2O4S [M+Na+] 363.0177, found 363.0177; IR (neat) 3314 cm-1

General procedure for thioether synthesis:

Method A via thiol and base:

To a dry roundbottom flask equipped with magnetic stir bar was added thiol (1.20 equiv) and base (1.15 equiv). The flask was evacuated and backfilled with argon and DMF (0.50 M) was added. Sulfonamide (1.0 equiv) was added and the reaction was adjusted to the appropriate temperature. The reaction was stirred at the same temperature until completion as indicated by TLC. Upon completion, the reaction was cooled in an ice bath and water was added with continued stirring until solid precipitate began to form. The solid was collected by filtration and washed with water to give crude product that was purified by recrystallization from appropriate solvent.

Method B via copper thiolate:

To a roundbottom flask equipped with a magnetic stir bar was added sulfonamide (1.0 equiv), DMF (0.33 M) and copper(I) phenylmethanethiolate (1.1 equiv) prepared as previously described31 from copper(I) oxide and benyl mercaptan. The reaction mixture was adjusted to 100 o C in an oil bath and stirred at the same temperature until completion as indicated by TLC. Upon

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by filtration. The filtrate was then cooled in an ice bath with stirring and water was added until a solid precipitate formed. The solid was collected by filtration and washed with water to give crude product that was purified by recrystallization from the appropriate solvent.

2-(benzylthio)-N-isopropylbenzenesulfonamide. Following general procedure A, from 2chloro-N-isopropylbenzenesulfonamide (2.07 g, 7.4 mmol), sodium hydroxide (0.34 g, 8.5 mmol) and benzyl mercaptan (1.04 mL, 8.9 mmol) at 100 oC was obtained clean product after recrystallization from ethyl acetate and hexanes. White solid (1.48 g, 4.6 mmol, 62 % yield);

m.p. 88 - 90 oC; 1H NMR (400 MHz, CDCl3) δ 8.05 (d, J = 7.6 Hz, 1H), 7.44 – 7.37 (m, 2H), 7.36 – 7.20 (m, 6H), 5.34 (d, J = 7.2 Hz, 1H), 4.22 (s, 2H), 3.50 – 3.18 (m, 1H), 0.95 (d, J = 6.5 Hz, 6H); 13C NMR (101 MHz, CDCl3) δ 140.5, 136.3, 134.3, 132.4, 132.2, 130.0, 129.1, 128.7, 127.6, 126.7, 46.5, 39.5, 23.4; HRMS (ESI) Calcd for C16H20NO2S2 [M+H+] 322.0930, found 322.0931; IR (neat) 3340 cm-1 2-(benzylthio)-N-phenylbenzenesulfonamide. Following general procedure A, from 2-bromoN-phenylbenzenesulfonamide (2.41 g, 7.7 mmol), potassium hydroxide (0.50 g, 8.9 mmol) and

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recrystallization from ethanol. White solid (1.66 g, 4.7 mmol, 61 % yield); m.p. 116 - 117 oC; 1H NMR (600 MHz, CDCl3) δ 7.87 (dd, J = 7.9, 1.5 Hz, 1H), 7.48 (s, 1H), 7.39 (dd, J = 7.9, 1.3 Hz, 1H), 7.37 – 7.22 (m, 6H), 7.18 (td, J = 7.6, 1.3 Hz, 1H), 7.12 (dd, J = 8.5, 7.3 Hz, 2H), 7.07 – 6.98 (m, 1H), 6.92 (dd, J = 8.5, 1.2 Hz, 2H), 4.27 (s, 2H); 13C NMR (151 MHz, CDCl3) δ 138.2, 136.2, 134.4, 132.8, 132.0, 131.0, 129.1, 129.1, 128.8, 127.7, 126.6, 125.5, 121.9, 39.5; HRMS (ESI) Calcd for C19H18NO2S2 [M+H+] 356.0773, found 356.0767; IR (neat) 3254 cm-1 2-(benzylthio)-N-(2,6-dimethylphenyl)benzenesulfonamide. Following general procedure B, from 2-chloro-N-(2,6-dimethylphenyl)benzenesulfonamide (1.06 g, 3.1 mmol) and copper(I) phenylmethanethiolate (0.64 g, 3.4 mmol) was obtained clean product after recrystallization from ethyl acetate and hexanes. Yellow solid (0.77 g, 2.0 mmol, 65 % yield); m.p. 148 -149 oC; 1H NMR (400 MHz, CDCl3) δ 7.88 – 7.82 (m, 1H), 7.48 – 7.41 (m, 2H), 7.40 – 7.34 (m, 2H), 7.35 – 7.23 (m, 4H), 7.07 (dd, J = 8.4, 6.6 Hz, 1H), 6.99 (m, 3H), 4.31 (s, 2H), 2.05 (s, 6H); 13C NMR (101 MHz, CDCl3) δ 141.6, 138.1, 136.0, 135.0, 132.9, 132.5, 131.3, 129.1, 129.0, 128.8, 128.6, 127.9, 127.7, 126.6, 39.6, 18.8; HRMS (ESI) Calcd for C21H22NO2S2 [M+H+] 384.1092, found

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2-(benzylthio)-N-isopropyl-5-nitrobenzenesulfonamide. Following the general procedure A, from 2-chloro-N-isopropyl-5-nitrobenzenesulfonamide (1.40 g, 5.0 mmol), NaOH (0.23 g, 5.8 mmol) and benzyl mercaptan (0.71 mL, 6.0 mmol) at 0 oC was obtained clean product after recrystallization. Yellow solid (1.73 g, 4.7 mmol, 94 % yield); m.p. 135 - 138 oC; 1H NMR (600 MHz,CDCl3) δ 8.83 (d, J = 2.5 Hz, 1H), 8.25 (dd, J = 8.8, 2.5 Hz, 1H), 7.57 (d, J = 8.8 Hz, 1H), 7.43 – 7.27 (m, 5H), 5.14 (d, J = 7.6 Hz, 1H), 4.35 (s, 2H), 3.50 – 3.34 (m, 1H), 1.02 (d, J = 6.6 Hz, 6H); 13C NMR (151 MHz, CDCl3) δ 145.3, 144.8, 139.4, 134.6, 129.2, 129.0, 128.5, 128.4, 126.5, 125.2, 46.9, 38.2, 23.6; HRMS (ESI) Calcd for C16H18ClNaN2O4S2 [M+Na+] 389.0600, found 389.0599; IR (neat) 3298 cm-1 2-(benzylthio)-5-nitro-N-phenylbenzenesulfonamide. Following general procedure A, from 2chloro-5-nitro-N-phenylbenzenesulfonamide (2.13 g, 6.8 mmol), KOH (0.42 g, 7.5 mmol) and benzyl mercaptan (0.96 mL, 8.2 mmol) at 120 oC was obtained clean product after recrystallization from ethanol and water. Yellow solid (1.93 g, 4.8 mmol, 71 % yield); m.p. 159 oC; 1H NMR (600 MHz, CDCl3) δ 8.64 (d, J = 2.5 Hz, 1H), 8.17 (dd, J = 8.7, 2.5 Hz, 1H), 7.54 (d, J = 8.7 Hz, 1H), 7.40 – 7.36 (m, 2H), 7.36 – 7.28 (m, 4H), 7.15 (t, J = 7.9 Hz, 2H), 7.06 <

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144.5, 136.8, 135.2, 134.4, 129.5, 129.1, 128.9, 128.3, 128.3, 126.9, 126.1, 126.0, 121.8, 38.1;

HRMS (ESI) Calcd for C19H16ClNaN2O4S2 [M+Na+] 423.0444, found 423.0444; IR (neat) 3291 cm-1 2-(benzylthio)-N-(2,6-dimethylphenyl)-5-nitrobenzenesulfonamide. Following general procedure A, from 2-chloro-N-(2,6-dimethylphenyl)-5-nitrobenzenesulfonamide (2.50 g, 7.3 mmol), KOH (0.45 g, 8.1 mmol) and benzyl mercaptan (1.03 mL, 8.8 mmol) at 0 oC was obtained clean product after recrystallization from ethanol and water. Yellow solid (2.74 g, 6.4 mmol, 87 % yield); m.p. 177 - 179 oC; 1H NMR (600 MHz, CDCl3) δ 8.60 (d, J = 2.5 Hz, 1H), 8.25 (dd, J = 8.7, 2.5 Hz, 1H), 7.59 (d, J = 8.7 Hz, 1H), 7.46 – 7.36 (m, 2H), 7.37 – 7.25 (m, 3H), 7.08 (t, J = 7.5 Hz, 1H), 6.99 (d, J = 7.5 Hz, 2H), 6.76 (s, 1H), 4.37 (s, 2H), 2.02 (s, 6H); 13C NMR (151 MHz, CDCl3) δ 145.9, 144.6, 140.1, 138.2, 134.2, 132.0, 129.1, 129.0, 128.8, 128.5, 128.3, 128.0, 126.6, 124.4, 38.3, 18.7; HRMS (ESI) Calcd for C21H20NaN2O4S2 [M+Na+] 451.0757, found 451.0756; IR (neat) 3305 cm-1

General procedure for BDT synthesis:

Method A via benzyl thioether:

To a roundbottom flask or test tube equipped with a magnetic stir bar was added thioether (1.0 equiv) and toluene (0.50 M). To the stirred solution at room temperature was added slowly

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2 hours. Upon completion, the reaction was allowed to cool to room temperature and concentrated to give crude product that was purified by recrystallization from an appropriate solvent.

Method B via disproportionation of disulfide:

To a round bottom flask equipped with a magnetic stir bar is added disulfide (1.0 equiv), oxidation catalyst (5 mol %) and either DMF or DMSO solvent (0.10 M). The reaction is heated to 100 oC in an oil bath until completion as indicated by TLC. Upon completion, the reaction was cooled to room temperature and water was added slowly until solid precipitate forms. The crude solid was collected by filtration, washed thoroughly with water and dried overnight to give the desired BDT that was purified by recrystallization from appropriate solvent when needed.

2-phenyl-2H-benzo[d][1,3,2]dithiazole 1,1-dioxide. Following method A, from 2-(benzylthio)N-phenylbenzenesulfonamide (2.32 g, 6.5 mmol) and sulfuryl chloride (0.63 mL, 7.9 mmol) was obtained clean product after recrystallization from ethanol. Pale yellow solid. (1.08 g, 4.1 mmol, 63 % yield); m.p. 152 - 153 oC; 1H NMR (600 MHz, CDCl3) δ 7.76 (d, J = 7.6 Hz, 1H), 7.65 (td, J = 7.8, 1.2 Hz, 1H), 7.49 (d, J = 8.0 Hz, 1H), 7.43 (td, J = 7.6, 0.9 Hz, 1H), 7.36 – 7.27 (m, 5H);

13 C NMR (75 MHz, CDCl3) δ 141.2, 138.8, 133.4, 130.1, 129.3, 128.5, 127.4, 125.7, 124.0,

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2-(2,6-dimethylphenyl)-2H-benzo[d][1,3,2]dithiazole 1,1-dioxide. Following method A, from 2-(benzylthio)-N-(2,6-dimethylphenyl)benzenesulfonamide (2.40 g, 6.3 mmol) and sulfuryl chloride (0.60 mL, 7.5 mmol) was obtained clean product after recrystallization from toluene.

White solid (1.13 g,3.9 mmol, 62 % yield); m.p. 165 -166 oC; 1H NMR (400 MHz, CDCl3) δ 7.86 (dd, J = 7.9, 1.1 Hz, 1H), 7.62 (tt, J = 7.4, 1.1 Hz, 1H), 7.49 – 7.37 (m, 2H), 7.20 (dd, J = 8.3, 6.8 Hz, 1H), 7.10 (d, J = 7.5 Hz, 2H), 2.26 (s, 6H); 13C NMR (100 MHz, CDCl3) δ 140.5, 136.9, 134.6, 132.6, 130.8, 129.8, 129.2, 126.8, 122.6, 121.7, 18.8; HRMS (ESI) Calcd for C14H13NO2S2 [M+H+] 292.0466, found 292.0458 2-isopropyl-6-nitro-2H-benzo[d][1,3,2]dithiazole 1,1-dioxide. Following method A, from 2benzylthio)-N-isopropyl-5-nitrobenzenesulfonamide (0.83 g, 2.3 mmol) and sulfuryl chloride (0.27 mL, 3.4 mmol) was obtained clean product after recrystallization from ethanol and water.

Yellow solid (0.45 g, 1.6 mmol, 72 % yield); m.p. 156 - 157 oC; 1H NMR (300 MHz, CDCl3) δ 8.58 (d, J = 2.1 Hz, 1H), 8.43 (dd, J = 8.6, 2.1 Hz, 1H), 7.56 (d, J = 8.6 Hz, 1H), 4.37 (hept, J =



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