3384 J. Am. Chem. Soc., Vol. 122, No. 14, 2000
Baxter et al.
with water and brine and dried over sodium sulfate. The solvent was
removed under vacuum, and the residue was purified by column
chromatography (ethyl acetate/hexane, 2:3; Rf 0.17) to yield a pale
yellow oil (1.24 g, 53%). IR (KBr), νmax/cm-1: 3386, 2964, 2890, 1495,
1339, 1302, 1145, 1024, 759, 697. 1H NMR (DMSO-d6), δ: 3.26 (2H,
t, J 6.5 Hz, CH2SO2), 3.80 (2H, t, J 6.5 Hz, CH2OH), 4.96 (1H, b s,
OH), 7.24 (5H, m, Ar H), 9.70 (1H, b s, NH). GC-MS, m/z: 201
(M+), 157, 120, 106, 93, 65.
Hz, MsOCH), 4.48 (1H, ABX, J 5 and 11 Hz, MsOCH), 7.24 (5H, m,
Ar H), 10.06 (1H, br s, NH). GC-MS, m/z: 293 (M+), 197, 132, 104,
93, 79, 65.
N-(3-Chlorophenyl)-2-hydroxyethanesulfonamide Mesylate. Mp
83-84 °C dec. IR (KBr), νmax/cm-1: 3294, 3028, 2939, 1596, 1463,
1
1340, 1327, 1173, 1154, 969, 941, 904, 804, 783, 742, 681. H NMR
(DMSO-d6), δ: 3.18 (3H, s, MeSO2), 3.65 (2H, t, J 6 Hz, CH2SO2),
4.49 (2H, t, J 6 Hz, MsOCH2), 7.19 (3H, m, Ar H), 7.37 (1H, m, Ar
H), 10.28 (1H, s, NH). GC-MS, m/z: 313-315 (M+), 217-219, 187-
189, 125-127, 99, 79.
N-Phenyl-2-hydroxy-1-phenylethanesulfonamide Mesylate. Mp
139-140 °C dec. IR (KBr), νmax/cm-1: 3278, 3025, 2938, 1598, 1496,
1350, 1175, 1152, 964, 917, 811, 753, 697. 1H NMR (CDCl3), δ: 2.97
(3H, s, MeSO2), 4.58 (1H, ABX, J 6.5 Hz, CHSO2), 4.72 (1H, ABX,
J 6.5 and 11 Hz, MsOCH), 4.97 (1H, ABX, J 6.5 and 11 Hz, MsOCH),
6.45 (1H, br s, NH), 7.26 (10H, m, Ar H).
2-Phenyl-1,2-thiazetidine 1,1-Dioxide. N-Phenyl-2-hydroxyethane-
sulfonamide mesylate (1.8 g, 6.45 mmol) was added to a stirred
suspension of potassium carbonate (2.67 g, 19.35 mmol) in dry DMSO
(30 mL) under nitrogen. The reaction mixture was heated for 1 h at 60
°C, cooled, and poured into water (40 mL). The organics were extracted
with ethyl acetate (3 × 75 mL), washed with water and brine, and
dried over sodium sulfate, and the solvent was removed under vacuum.
The residue was purified by column chromatography (dichloromethane;
Rf 0.42) to yield a white solid (0.5 g, 42%). Mp: 128-129 °C (lit.43
132 °C). IR (Nujol), νmax/cm-1: 3073, 3057, 3030, 1601, 1499, 1313,
1202, 1179, 1150, 1088, 1038, 962, 774, 760, 695. 1H NMR (CDCl3),
δ: 3.66 (2H, t, J 6.5 Hz, CH2N), 4.23 (2H, t, J 6.5 Hz, CH2SO2), 6.90
(2H, d, J 8 Hz, Ar H), 7.06 (1H, m, Ar H), 7.33 (2H, m, Ar H). GC-
MS, m/z: 183 (M+), 118, 104, 91, 77, 64. Anal. Calcd for C8H9NO2S:
C, 52.45; H, 4.95; N, 7.65; S, 17.50. Found: C, 52.40; H, 5.05; N,
7.50; S, 17.50.
N-(4-Chlorophenyl)-2-hydroxyethanesulfonamide. Mp: 95 °C. IR
(KBr), νmax/cm-1: 3422, 3144, 3061, 2935, 2872, 1490, 1326, 1138,
1066, 842, 819, 733, 713. 1H NMR (DMSO-d6), δ: 3.25 (2H, t, J 6.5
Hz, CH2SO2), 3.75 (2H, t, J 6.5 Hz, CH2OH), 4.94 (1H, br s, OH),
7.22 (2H, d, J 9 Hz, Ar H), 7.38 (2H, d, J 9 Hz, Ar H); 9.89 (1H, br
s, NH). GC-MS, m/z: 235-237 (M+), 140-141, 126, 99-101, 90.
N-(4-Methylphenyl)-2-hydroxyethanesulfonamide. Mp: 165 °C.
IR (KBr), νmax/cm-1: 3431, 3193, 2961, 2926, 2882, 1511, 1390, 1329,
1296, 1222, 1162, 1136, 1069, 1009, 950, 918, 815, 717, 703. 1H NMR
(DMSO-d6), δ: 2.26 (3H, s, Me); 3.17 (2H, t, J 6.5 Hz, CH2SO2), 3.72
(2H, t, J 6.5 Hz, CH2OH), 4.92 (1H, br s, OH), 7.13 (4H, m, Ar H),
9.56 (1H, br s, NH). GC-MS, m/z: 215 (M+), 134, 120, 106, 79.
N-Phenyl-2-hydroxypropanesulfonamide. IR (KBr), νmax/cm-1
:
3497, 3264, 3087, 2980, 2941, 2890, 1599, 1496, 1416, 1323, 1300,
1
1220, 1148, 1045, 926, 756, 697. H NMR (DMSO-d6), δ: 1.28 (3H,
d, J 6.5 Hz, Me), 3.15 (1H, m, CHSO2), 3.45 (1H, ABX, J 8 and 11
Hz, CHOH), 3.86 (1H, ABX, J 11 and 4.5 Hz, CHOH), 5.14 (1H, br
s, OH), 7.26 (5H, m, Ar H), 9.49 (1H, br s, NH). GC-MS, m/z: 215
(M+), 152, 93, 77, 65.
N-(3-Chlorophenyl)-2-hydroxyethanesulfonamide. Mp: 70 °C. IR
(KBr), νmax/cm-1: 3417, 3194, 2959, 1596, 1326, 1136, 1066, 949, 789,
1
723. H NMR (DMSO-d6), δ: 3.28 (2H, t, J 6.5 Hz, CH2SO2), 3.74
(2H, t, J 6.5 Hz, CH2OH), 4.94 (1H, br s, OH), 7.23 (4H, m, Ar H),
10.00 (1H, br s, NH). GC-MS, m/z: 235-237 (M+), 127-129, 91,
73, 63.
N-(4-Chlorophenyl)-1,2-thiazetidine 1,1-Dioxide. Mp: 208 °C. IR
(KBr), νmax/cm-1: 3038, 2977, 2911, 1601, 1497, 1422, 1335, 1304,
N-Phenyl-2-hydroxy-1-phenylethanesulfonamide. Mp: 106-108
1
°C. IR (KBr), νmax/cm-1: 3502, 3266, 3064, 2974, 2895, 1599, 1495,
1205, 1156, 813, 792, 736. H NMR (CDCl3), δ: 3.62 (2H, t, J 6.5,
1
CH2N), 4.23 (2H, t, J 6.5, CH2SO2), 6.78 (2H, m, Ar H), 7.22 (2H, m,
Ar H). GC-MS, m/z: 217-219 (M+), 138-140, 125-127, 111-113,
90, 75, 63. Anal. Calcd for C8H8ClNO2S: C, 44.14; H, 3.70; N, 6.43;
S, 14.73. Found: C, 44.00; H, 3.65; N, 6.36, S, 14.161.
1418, 1339, 1300, 1147, 1058, 928, 754, 696. H NMR (DMSO-d6),
δ: 3.99 (1H, ABX, J 9 and 11 Hz, CHOH); 4.20 (1H, ABX, J 4.5 and
11 Hz, CHOH), 4.35 (1H, ABX, J 4.5 and 9 Hz, CHSO2), 5.05 (1H,
br s, OH), 7.28 (10H, m, Ar H), 9.84 (1H, br s, NH).
N-(4-Methylphenyl)-1,2-thiazetidine 1,1-Dioxide. Mp: 143-145
N-Phenyl-2-hydroxyethanesulfonamide Mesylate. N-Phenyl-2-
hydroxyethanesulfonamide (2.77 g, 13.78 mmol) was dissolved in dry
dichloromethane (30 mL) under nitrogen. Mesyl chloride (1.07 mL,
13.78 mmol) and triethylamine (1.92 mL, 13.78 mmol) were added to
the solution, and the mixture was stirred at 0 °C for 2 h. The organics
were washed with dilute hydrochloric acid, water, and brine and dried
over sodium sulfate, and the solvent was removed under vacuum. The
residue was purified by trituration from ether to yield a white solid
(2.4 g, 62%). Mp: 94-95 °C dec. IR (KBr), νmax/cm-1: 3274, 3024,
2938, 1478, 1416, 1342, 1169, 1152, 1069, 988, 968, 915, 802, 758,
°C. IR (Nujol), νmax/cm-1: 3036, 1515, 1474, 1317, 1296, 1205, 1192,
1
1152, 1031, 958, 817, 805, 763. H NMR (CDCl3), δ: 2.30 (3H, s,
MeAr), 3.67 (2H, t, J 6.5 Hz, CH2N), 4.25 (2H, t, J 6.5 Hz, CH2SO2),
6.83 (2H, m, Ar H), 7.13 (2H, m, Ar H). GC-MS, m/z: 197 (M+),
149, 130, 118, 105, 91, 77, 65. Anal. Calcd for C9H11NO2S: C, 54.80;
H, 5.60; N, 7.10; S, 16.25. Found: C, 54.60; H, 5.60; N, 7.00; S, 15.90.
N-Phenyl-4-methyl-1,2-thiazetidine 1,1-Dioxide. Mp 124-125 °C.
IR (Nujol), νmax/cm-1: 3055, 1600, 1496, 1321, 1310, 1203, 1173, 1146,
1
1087, 964, 756, 694. H NMR (CDCl3), δ: 1.68 (3H, d, J 7 Hz, Me),
1
743, 696. H NMR (DMSO-d6), δ: 3.11 (3H, s, MeSO2), 3.59 (2H, t,
3.23 (1H, t, J 5 Hz, CH2N), 3.86 (1H, dd, J 5 and 8 Hz, CH2N), 4.55
(1H, m, J 5, 7, and 8 Hz, CHSO2), 6.90 (2H, m, Ar H), 7.06 (1H, m,
Ar H), 7.33 (2H, m, Ar H). Anal. Calcd for C9H11NO2S: C, 54.80; H,
5.60; N, 7.10; S, 16.25. Found: C, 54.80; H, 5.65; N, 7.00; S, 16.10.
N-(3-Chlorophenyl)-1,2-thiazetidine 1,1-Dioxide. Mp: 81-82 °C.
IR (Nujol), νmax/cm-1: 3048, 1597, 1481, 1315, 1200, 1152, 1078, 994,
769, 678. 1H NMR (400 MHz, CDCl3), δ: 3.71 (2H, t, J 6.5 Hz, CH2N),
4.30 (2H, t, J 6.5 Hz, CH2SO2), 6.85 (1H, m, Ar H), 6.89 (1H, m, Ar
H), 7.07 (1H, m, Ar H), 7.28 (1H, m, Ar H). 13C NMR (100 MHz,
CDCl3), δ: 33.2, 57.5, 113.4, 115, 123.4, 130.6, 135.4, 139.4. GC-
MS, m/z: 217-219 (M+), 138-140, 125-127, 111-113, 91, 63. Anal.
Calcd for C8H8ClNO2S: C, 44.15; H, 3.70; N, 6.45; S, 14.75. Found:
C, 44.10; H, 3.70; N, 6.35; S, 14.55.
J 6 Hz, CH2SO2), 4.59 (2H, t, J 6 Hz, MsOCH2), 7.19 (5H, m, Ar H),
8.82 (1H, br s, NH). GC-MS, m/z: 183 (M+ - MeSO3H), 118, 92, 65.
N-(4-Chlorophenyl)-2-hydroxyethanesulfonamide Mesylate. Mp:
113-114 °C dec. IR (KBr), νmax/cm-1: 3264, 3027, 3017, 2987, 2936,
1492, 1346, 1335, 1177, 1148, 989, 964, 821, 794, 711. 1H NMR
(DMSO-d6), δ: 3.19 (3H, s, MeSO2), 3.60 (2H, t, J 6 Hz, CH2SO2),
4.45 (2H, t, J 6 Hz, MsOCH2), 7.22 (2H, m, Ar H), 7.42 (2H, m, Ar
H), 10.17 (1H, br s, NH). GC-MS, m/z: 313-315 (M+), 217-219,
138-140, 126, 99-101, 79.
N-(4-Methylphenyl)-2-hydroxyethanesulfonamide Mesylate. Mp:
84-85 °C dec. IR (KBr), νmax/cm-1: 3269, 3088, 3022, 3014, 2986,
2938, 1513, 1478, 1398, 1335, 1304, 1176, 1148, 981, 964, 916, 883,
814, 794, 729, 704. 1H NMR (DMSO-d6), δ: 2.26 (3H, s, MeAr), 3.19
(3H, s, MeSO2), 3.51 (2H, t, J 6 Hz, CH2SO2), 4.48 (2H, t, J 6 Hz,
MsOCH2), 7.13 (4H, s, Ar H), 9.86 (1H, br s, NH). GC-MS, m/z:
293 (M+), 197, 133, 120, 106, 91, 79.
N-Phenyl-4-phenyl-1,2-thiazetidine 1,1-Dioxide. Mp: 155-157 °C.
IR (Nujol), νmax/cm-1: 3058, 3038, 1596, 1492, 1472, 1322, 1316, 1301,
1
1181, 1148, 1087, 1030, 957, 768, 750, 730, 696. H NMR (CDCl3),
δ: 4.58 (1H, ABX, J 7 Hz, CHSO2), 4.72 (1H, ABX, J 7 and 11 Hz,
CH2N), 4.97 (1H, ABX, J 7 and 11 Hz, CH2N), 7.25 (10H, m, Ar H).
Anal. Calcd for C14H13NO2S: C, 64.85; H, 5.05; N, 5.40; S, 12.35.
Found: C, 64.70; H, 5.05; N, 5.35; S, 12.30.
N-Phenyl-2-hydroxypropanesulfonamide Mesylate: Mp: 114-
115 °C dec. IR (KBr), νmax/cm-1: 3232, 3024, 2937, 2909, 1491, 1423,
1359, 1334, 1288, 1175, 1154, 1097, 979, 961, 948, 929, 840, 762,
1
696. H NMR (DMSO-d6), δ: 1.33 (3H, d, J 6.5 Hz, MeCH), 3.19
N-(4-Hydroxyphenyl)-1,2-thiazetidine 1,1-Dioxide. Mp: 162-165
(3H, s, MeSO3), 3.54 (1H, m, CHSO2), 4.35 (1H, ABX, J 6 and 11
°C dec. IR (Nujol), νmax/cm-1: 3424, 3155, 3048, 1513, 1319, 1260,