3874 J. Agric. Food Chem., Vol. 53, No. 10, 2005
Li et al.
3
Data for Carbamic Acid, (1,2,3-Thiadiazole-4-ylcarbo-
nyl)-, Heptyl Ester (5). Yield, 48%; white needle crystal; mp
88-90 °C. 1H NMR: δ 0.96 (t, 3H, CH3), 1.12-1.92 (m, 10H,
(m, 28H, CH2), 4.26 (t, 2H, OCH2, J ) 7.2 Hz), 9.37 (br, s,
2H, Het-H, NH). IR (KBr): 3320 (NH), 3100, 2900, 2850 (C-
H), 1770 (CO), 1700 (CO), 1510, 1465 (CH2), 1400, 1230 (CN),
1180, 950, 770 cm-1. MS m/z (relative intensity): 398 (M +
1, 1), 370 (1), 336 (1), 275 (1), 174 (53), 148 (11), 130 (4),
113 (8), 97 (12), 85 (23), 69 (40), 57 (100), 43 (96). Anal. calcd
for C20H35N3O3S: C, 60.42; H, 8.87; N, 10.57. Found: C, 60.44;
H, 8.76; N, 10.52.
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CH2), 4.24 (t, 2H, OCH2, J ) 7.2 Hz), 9.92 (s, 1H, Het-H),
11.28 (1H, NH). IR (KBr): 3320 (NH), 3105, 2900, 2850 (C-
H), 1770 (CO), 1700 (CO), 1510, 1465 (CH2), 1400, 1230 (CN),
1180, 765 cm-1. Anal. calcd for C11H17N3O3S: C, 48.69; H,
6.32; N, 15.49. Found: C, 48.85; H, 6.37; N, 16.57.
Data for Carbamic Acid, (1,2,3-Thiadiazole-4-ylcarbo-
nyl)-, Octyl Ester (6). Yield, 48%; white powder crystal; mp
95-97 °C. 1H NMR: δ 0.84 (t, 3H, CH3, 3J ) 7.2 Hz), 1.04-
1.76 (m, 12H, CH2), 4.12 (t, 2H, OCH2, 3J ) 7.2 Hz), 9.84 (s,
1H, Het-H), 11.08 (1H, NH). IR (KBr): 3380 (NH), 3120,
2930, 2850 (C-H), 1775 (CO), 1700 (CO), 1510, 1465 (CH2),
1400, 1230 (CN), 1155, 940, 775 cm-1. Anal. calcd for
C12H19N3O3S: C, 50.51; H, 6.71; N, 14.73. Found: C, 50.78;
H, 6.56; N, 14.72.
Data for Carbamic Acid, (1,2,3-Thiadiazole-4-ylcarbo-
nyl)-, ω-Bromo-decyl Ester (13). Yield, 42%; white flake
crystal; mp 88-89 °C. 1H NMR: δ 1.20-2.00 (m, 16H, CH2),
3.40 (t, 2H, CH2Br, J ) 7.2 Hz), 4.28 (t, 2H, OCH2, J ) 7.2
Hz), 9.38 (s, 1H, Het-H), 9.46 (s, 1H, NH). IR (KBr): 3350
(NH), 3100, 2900, 2850 (C-H), 1770 (CO), 1700 (CO), 1510,
1465 (CH2), 1400, 1230 (CN), 1180, 950, 770 cm-1. Anal. calcd
for C14H22N3O3SBr: C, 42.86; H, 5.65; N, 10.71. Found: C,
42.98; H, 5.76; N, 10.64.
Data for Carbamic Acid, (1,2,3-Thiadiazole-4-ylcarbo-
nyl)-, Nonyl Ester (7). Yield, 69%; white flake crystal; mp
96-98 °C. 1H NMR: δ 0.88 (t, 3H, CH3, 3J ) 7.2 Hz), 1.12-
1.86 (m, 14H, CH2), 4.28 (t, 2H, OCH2, 3J ) 7.2 Hz), 9.40 (br,
2H, Het-H, NH). IR (KBr): 3320 (NH), 3110, 2950, 2850 (C-
H), 1770 (CO), 1700 (CO), 1510, 1465 (CH2), 1400, 1230 (CN),
1175, 950, 770 cm-1. Anal. calcd for C13H21N3O3S: C, 52.15;
H, 7.07; N, 14.04. Found: C, 52.18; H, 6.76; N, 14.05.
Data for Carbamic Acid, (1,2,3-Thiadiazole-4-ylcarbo-
nyl)-, and Decayl Ester (8). Yield, 45%; white needle crystal;
Data for Carbamic Acid, (1,2,3-Thiadiazole-4-ylcarbo-
nyl)-, ω-Bromo-dodecyl Ester (14). Yield, 35%; white flake
crystal; mp 89-91 °C. 1H NMR: δ 1.20-2.00 (m, 20H, CH2),
3.40 (t, 2H, CH2Br, J ) 7.2 Hz), 4.28 (t, 2H, OCH2, J ) 7.2
Hz), 9.38 (s, 1H, Het-H), 9.46 (s, 1H, NH). IR (KBr): 3340
(NH), 3100, 2900, 2850 (C-H), 1770 (CO), 1700 (CO), 1510,
1460 (CH2), 1400, 1270 (CN), 1230, 1175, 950, 770 cm-1. Anal.
calcd for C16H26N3O3SBr: C, 45.72; H, 6.23; N, 10.00. Found:
C, 45.92; H, 6.30; N, 9.96.
Data for Carbamothioic Acid, (1,2,3-Thiadiazole-4-ylcar-
bonyl)-, S-Propyl Ester (15). Yield, 62%; white needle crystal;
mp 101-103 °C. 1H NMR: δ 1.00 (t, 3H, CH3, 3J ) 7.2 Hz),
1.44-1.92 (m, 2H, CH2), 2.96 (t, 2H, SCH2, J ) 7.2 Hz), 9.36
(s, 1H, Het-H), 9.88 (s, 1H, NH). IR (KBr): 3380 (NH), 3200,
3080, 2950, 2850 (C-H), 1705 (CO), 1650 (CO), 1500, 1400,
1300 (CN), 1260, 855, 800, 745 cm-1. MS m/z (relative
intensity): 231 (M+, 2), 189 (1), 156 (34), 130 (4), 113 (50),
90 (4), 85 (26), 70 (9), 57 (58), 43 (100). Anal. calcd for
C7H9N3O2S2: C, 36.35; H, 3.92; N, 18.17. Found: C, 36.20;
H, 3.86; N, 18.12.
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mp 100-101 °C. H NMR: δ 0.88 (t, 3H, CH3), 1.16-1.92
(m, 16H, CH2), 4.28 (t, 2H, OCH2, 3J ) 7.2 Hz), 9.38 (br, 2H,
Het-H, NH). IR (KBr): 3320 (NH), 3105, 2950, 2850 (C-
H), 1775 (CO), 1700 (CO), 1510, 1470 (CH2), 1400, 1230 (CN),
1180, 770, 640 cm-1. MS m/z (relative intensity): 314 (M + 1,
5), 286 (1), 242 (1), 214 (1), 174 (28), 130 (30), 113 (6), 85
(17), 69 (23), 57 (74), 43 (100). Anal. calcd for C14H23N3O3S:
C, 53.65; H, 7.40; N, 13.41. Found: C, 53.64; H, 7.27; N, 13.43.
Data for Carbamic Acid, (1,2,3-Thiadiazole-4-ylcarbo-
nyl)-, Undecyl Ester (9). Yield, 42%; white powder crystal;
1
mp 102-103 °C. H NMR: δ 0.86 (t, 3H, CH3), 1.12-1.80
Data for Carbamothioic Acid, (1,2,3-Thiadiazole-4-ylcar-
bonyl)-, S-Butyl Ester (16). Yield, 38%; white flake crystal;
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(m, 18H, CH2), 4.16 (t, 2H, OCH2, J ) 7.2 Hz), 9.88 (s, 1H,
1
3
Het-H), 11.20 (s, 1H, NH). IR (KBr): 3320 (NH), 3105, 2900,
2850 (C-H), 1770 (CO), 1700 (CO), 1510, 1465 (CH2), 1400,
mp 80-82 °C. H NMR: δ 0.96 (t, 3H, CH3, J ) 7.2 Hz),
1.12-1.92 (m, 4H, CH2), 3.00 (t, 2H, SCH2, J ) 7.2 Hz), 9.40
(s, 1H, Het-H), 9.92 (s, 1H, NH). IR (KBr): 3400 (NH), 3200,
2900, 2850 (C-H), 1705 (CO), 1650 (CO), 1490, 1400, 1300
(CN), 1260, 860, 750 cm-1. Anal. calcd for C8H11N3O2S2: C,
39.17; H, 4.52; N, 17.13. Found: C, 39.61; H, 4.62; N, 16.98.
Data for Carbamothioic Acid, (1,2,3-Thiadiazole-4-ylcar-
bonyl)-, S-Hexyl Ester (17). Yield, 68%; white needle crystal;
1230 (CN), 1180, 950, 770 cm-1
. Anal. calcd for
C15H25N3O3S: C, 55.02; H, 7.70; N, 12.84. Found: C, 54.96;
H, 7.66; N, 12.88.
Data for Carbamic Acid, (1,2,3-Thiadiazole-4-ylcarbo-
nyl)-, Cyclohexyl Ester (10). Yield, 56%; white powder crystal;
mp 143-145 °C. 1H NMR: δ 1.12-2.16 (m, 10H, CH2), 4.56-
4.96 (m, 1H, CH), 9.92 (s, 1H, Het-H), 11.20 (s, 1H, NH). IR
(KBr): 3380 (NH), 3100, 2900, 2850 (C-H), 1775 (CO), 1710
(CO), 1400, 1230 (CN), 1155, 770 cm-1. Anal. calcd for
C10H13N3O3S: C, 47.05; H, 5.14; N, 16.4. Found: C, 47.58;
H, 5.34; N, 16.45.
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mp 78-80 °C. H NMR: δ 0.88 (t, 3H, CH3, J ) 7.2 Hz),
1.04-1.84 (m, 8H, CH2), 2.96 (t, 2H, SCH2, J ) 7.2 Hz), 9.36
(s, 1H, Het-H), 9.92 (s, 1H, NH). IR (KBr): 3400 (NH), 3200,
3100, 2950, 2850 (C-H), 1720 (CO), 1650 (CO), 1500, 1440,
1260, 850, 750 cm-1. Anal. calcd for C10H15N3O2S2: C, 43.94;
H, 5.53; N, 15.37. Found: C, 44.05; H, 5.44; N, 15.45.
Data for Carbamothioic Acid, (1,2,3-Thiadiazole-4-ylcar-
bonyl)-, S-Heptyl Ester (18). Yield, 52%; white flake crystal,
Data for Carbamic Acid, (1,2,3-Thiadiazole-4-ylcarbo-
nyl)-, Tetradecyl Ester (11). Yield, 41%; white powder crystal;
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mp 109-110 °C. H NMR: δ 0.88 (t, 3H, CH3), 1.16-1.80
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1
(m, 24H, CH2), 4.16 (t, 2H, OCH2, J ) 7.2 Hz), 9.88 (s, 1H,
mp 88-90 °C. H NMR: δ 0.84 (t, 3H, CH3), 1.04-1.84 (m,
Het-H), 11.19 (s, 1H, NH). IR (KBr): 3320 (NH), 3110, 2900,
2850 (C-H), 1775 (CO), 1700 (CO), 1510, 1460 (CH2), 1400,
10H, CH2), 2.96 (t, 2H, SCH2, J ) 7.2 Hz), 9.36 (s, 1H, Het-
H), 9.88 (s, 1H, NH). IR (KBr): 3400 (NH), 3200, 3080, 2900,
2850 (C-H), 1705 (CO), 1645 (CO), 1500, 1440, 1300 (CN),
1260, 860, 750 cm-1. Anal. calcd for C11H17N3O2S2: C, 45.97;
H, 5.96; N, 14.62. Found: C, 46.12; H, 5.98; N, 14.18.
Data for Carbamothioic Acid, (1,2,3-Thiadiazole-4-ylcar-
bonyl)-, S-Octyl Ester (19). Yield, 58%; white flake crystal;
1230 (CN), 1185, 955, 770 cm-1
. Anal. calcd for
C18H31N3O3S: C, 58.51; H, 8.46; N, 11.37. Found: C, 58.50:
H, 8.26; N, 11.06.
Data for Carbamic Acid, (1,2,3-Thiadiazole-4-ylcarbo-
nyl)-, Hexadecyl Ester (12). Yield, 37%; white powder crystal;
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mp 107-108 °C. H NMR: δ 0.86 (t, 3H, CH3), 1.08-1.80
mp 75-77 °C. H NMR: δ 0.88 (t, 3H, CH3), 1.12-1.84 (m,