2006
Helvetica Chimica Acta – Vol. 94 (2011)
5-Chloro-2-[(ethylsulfanyl)methyl]-N-(3-methoxyphenyl)benzamide (5k). White solid. M.p. 79 – 818
(hexane/CH2Cl2). IR (KBr): 3293, 1651, 1609. 1H-NMR: 1.28 (t, J ¼ 7.3, 3 H); 2.58 (q, J ¼ 7.3, 2 H); 3.84
(s, 3 H); 3.90 (s, 2 H); 6.72 (dd, J ¼ 7.8, 1.8, 1 H); 7.14 (dd, J ¼ 7.8, 0.9, 1 H); 7.25 – 7.29 (m, 2 H); 7.38 (dd,
J ¼ 8.2, 2.3, 1 H); 7.44 (t, J ¼ 1.8, 1 H); 7.64 (d, J ¼ 2.3, 1 H); 8.65 (br. s, 1 H). Anal. calc. for C17H18ClNO2S
(335.85): C 60.80, H 5.40, N 4.17; found: C 60.52, H 5.45, N 3.93.
N-Aryl-2-[(aryl- or alkylsulfinyl)methyl]benzamides 2. These compounds were prepared by treating
5 (2.0 mmol) with NaIO4 (0.43 g, 2.0 mmol) in MeOH/H2O 9 :1 (10 ml; v/v) at r.t.
N-Phenyl-2-[(phenylsulfinyl)methyl]benzamide (2a). White solid. M.p. 164 – 1688 (hexane/CH2Cl2).
IR (KBr): 3235, 1660, 1031. 1H-NMR: 4.30 (d, J ¼ 13.3, 1 H); 4.35 (d, J ¼ 13.3, 1 H); 7.01 (d, J ¼ 7.3, 1 H);
7.17 (t, J ¼ 7.3, 1 H); 7.36 – 7.41 (m, 3 H); 7.44 (ddd, J ¼ 7.8, 7.3, 1.4, 1 H); 7.48 – 7.53 (m, 3 H); 7.58 (dd, J ¼
7.8, 1.8, 2 H); 7.73 (dd, J ¼ 7.8, 0.9, 1 H); 7.87 (d, J ¼ 8.2, 2 H); 9.98 (br. s, 1 H). Anal. calc. for C20H17NO2S
(335.42): C 71.62, H 5.11, N 4.18; found: C 71.50, H 5.26, N 4.04.
N-(4-Methylphenyl)-2-[(phenylsulfinyl)methyl]benzamide (2b). White solid. M.p. 171 – 1738 (hex-
ane). IR (KBr): 3235, 1667, 1030. 1H-NMR: 2.36 (s, 3 H); 4.28 (d, J ¼ 12.8, 1 H); 4.34 (d, J ¼ 12.8, 1 H);
7.00 (d, J ¼ 7.3, 1 H); 7.19 (d, J ¼ 8.2, 2 H); 7.37 (ddd, J ¼ 7.8, 7.3, 1.4, 1 H); 7.43 (ddd, J ¼ 7.8, 7.3, 1.4, 1 H);
7.48 – 7.54 (m, 3 H); 7.57 (dd, J ¼ 7.8, 1.4, 2 H); 7.72 (dd, J ¼ 7.8, 1.4, 1 H); 7.74 (d, J ¼ 8.2, 2 H); 9.84 (br. s,
1 H). Anal. calc. for C21H19NO2S (349.45): C 72.18, H 5.48, N 4.01; found: C 72.17, H 5.67, N 3.94.
N-(4-Methoxyphenyl)-2-[(phenylsulfinyl)methyl]benzamide (2c). White solid. M.p. 131 – 1338
(hexane/CH2Cl2); IR (KBr) 3258, 1649, 1609, 1028. 1H-NMR: 3.84 (s, 3 H); 4.29 (d, J ¼ 13.3, 1 H);
4.34 (d, J ¼ 13.3, 1 H); 6.93 (d, J ¼ 9.2, 2 H); 7.01 (d, J ¼ 7.8, 1 H); 7.37 (dd, J ¼ 7.8, 7.3, 1 H); 7.43 (dd, J ¼
7.8, 7.3, 1 H); 7.49 – 7.53 (m, 3 H); 7.56 (d, J ¼ 7.8, 2 H); 7.72 (d, J ¼ 7.8, 1 H); 7.78 (d, J ¼ 9.2, 2 H); 9.85 (br.
s, 1 H). Anal. calc. for C21H19NO3S (365.45): C 69.02, H 5.24, N 3.83; found: C 68.83, H 5.28, N 3.68.
2-{[(4-Chlorophenyl)sulfinyl]methyl}-N-phenylbenzamide (2d). White solid. M.p. 133 – 1358 (hex-
ane/CH2Cl2). IR (KBr): 3281, 3248, 1662, 1030. 1H-NMR: 4.27 (d, J ¼ 13.3, 1 H); 4.39 (d, J ¼ 13.3, 1 H);
7.03 (d, J ¼ 7.3, 1 H); 7.17 (dd, J ¼ 7.8, 7.3, 1 H); 7.38 – 7.50 (m, 8 H); 7.71 (dd, J ¼ 7.8, 1.4, 1 H); 7.81 (d, J ¼
8.2, 2 H); 9.60 (br. s, 1 H). Anal. calc. for C20H16ClNO2S (369.86): C 64.95, H 4.36, N 3.79; found: C 65.05,
H 4.45, N 3.61.
N-(4-Chlorophenyl)-2-{[(4-chlorophenyl)sulfinyl]methyl}benzamide (2e). White solid. M.p. 183 –
1848 (hexane/CH2Cl2). IR (KBr): 3271, 3242, 1661, 1030. 1H-NMR: 4.25 (d, J ¼ 13.3, 1 H); 4.36 (d, J ¼
13.3, 1 H); 6.99 (d, J ¼ 7.8, 1 H); 7.26 (dd, J ¼ 7.8, 7.3, 1 H); 7.35 (d, J ¼ 8.7, 2 H); 7.40 (ddd, J ¼ 7.8, 7.3,
1.4, 1 H); 7.44 – 7.50 (m, 4 H); 7.71 (d, J ¼ 7.8, 1 H); 7.79 (d, J ¼ 8.7, 2 H); 9.89 (br. s, 1 H). Anal. calc. for
C20H15Cl2NO2S (404.31): C 59.41, H 3.74, N 3.46; found: C 59.39, H 3.77, N 3.30.
2-[(Ethylsulfinyl)methyl]-N-phenylbenzamide (2f). White solid. M.p. 122 – 1248 (hexane/CH2Cl2).
1
IR (KBr): 3271, 3235, 1667, 1015. H-NMR: 1.40 (t, J ¼ 7.3, 3 H); 2.85 – 2.97 (m, 2 H); 4.03 (d, J ¼ 12.8,
1 H); 4.35 (d, J ¼ 12.8, 1 H); 7.12 (tt, J ¼ 7.3, 0.9, 1 H); 7.34 – 7.38 (m, 3 H); 7.45 (t, J ¼ 7.3, 1 H); 7.50 (t, J ¼
7.3, 1 H); 7.74 (d, J ¼ 7.3, 1 H); 7.81 (d, J ¼ 8.2, 2 H); 10.07 (br. s, 1 H). Anal. calc. for C16H17NO2S
(287.38): C 66.87, H 5.96, N 4.87; found: C 66.85, H 6.16, N 4.74.
N-(3,5-Dimethylphenyl)-2-[(ethylsulfinyl)methyl]benzamide (2g). White solid. M.p. 173 – 1758
1
(hexane/CH2Cl2). IR (KBr): 3235, 1665, 1009. H-NMR: 1.40 (t, J ¼ 7.3, 3 H); 2.32 (s, 6 H); 2.83 – 2.98
(m, 2 H); 4.04 (d, J ¼ 12.8, 1 H); 4.33 (d, J ¼ 12.8, 1 H); 6.78 (s, 1 H); 7.37 (dd, J ¼ 7.3, 1.4, 1 H); 7.43 – 7.46
(m, 3 H); 7.49 (td, J ¼ 7.3, 1.4, 1 H); 7.72 (dd, J ¼ 7.3, 1 H); 9.85 (br. s, 1 H). Anal. calc. for C18H21NO2S
(315.43): C 68.54, H 6.71, N 4.44; found: C 68.61, H 6.90, N 4.36.
2-[(Ethylsulfinyl)methyl]-N-(3-methoxyphenyl)benzamide (2h). White solid. M.p. 111 – 1138 (hex-
ane/CH2Cl2). IR (KBr): 3246, 1667, 1609, 1015. 1H-NMR: 1.40 (t, J ¼ 7.3, 3 H); 2.84 – 2.99 (m, 2 H); 3.83
(s, 3 H); 4.02 (d, J ¼ 12.8, 1 H); 4.36 (d, J ¼ 12.8, 1 H); 6.69 (dd, J ¼ 8.2, 1.8, 1 H); 7.24 (t, J ¼ 8.2, 1 H); 7.30
(d, J ¼ 8.2, 1 H); 7.37 (d, J ¼ 7.8, 1 H); 7.45 (ddd, J ¼ 7.8, 7.3, 0.9, 1 H); 7.50 (dd, J ¼ 7.8, 7.3, 1.4, 1 H); 7.59 (s,
1 H); 7.74 (d, J ¼ 7.8, 1 H); 10.09 (br. s, 1 H). Anal. calc. for C17H19NO3S (317.40): C 64.33, H 6.03, N 4.41;
found: C 64.17, H 5.95, N 4.35.
5-Chloro-2-[(ethylsulfinyl)methyl]-N-phenylbenzamide (2i). White solid. M.p. 130 – 1328 (hexane/
1
CH2Cl2). IR (KBr): 3235, 1661, 1005. H-NMR: 1.41 (t, J ¼ 7.3, 3 H); 2.84 – 2.99 (m, 2 H); 3.99 (d, J ¼
13.3, 1 H); 4.34 (d, J ¼ 13.3, 1 H); 7.14 (tt, J ¼ 7.3, 1.4, 1 H); 7.31 (d, J ¼ 8.2, 1 H); 7.36 (t, J ¼ 7.3, 2 H);
7.47 (dd, J ¼ 8.2, 2.3, 1 H); 7.73 (d, J ¼ 2.3, 1 H); 7.79 (d, J ¼ 7.3, 2 H); 10.13 (br. s, 1 H). Anal. calc. for
C16H16ClNO2S (321.82): C 59.71, H 5.01, N 4.35; found: C 59.55, H 5.19, N 4.47.