BENDJEDDOU et al., Orient. J. Chem., Vol. 32(2), 799-806 (2016)
801
N-(thiophen-2-yl methyl)-N’-(isobutyl)
sulfamide 3
for C11H19N3O2S: C, 51.33%; H, 7.44; S, 12.46%;
found: C, 51.48%; H, 7.59%; S, 12.61%.
Beige powder. Yield: 26%. M.p.: 151°C.
TLC: Rf = 0.77 (AcOEt / n-Hexane: 6/4). 1H NMR
(400 MHz, CDCl3, d, ppm): 1.06 (d, 6H, 2CH3); 2.00
(m, 1H, CH(CH3)2); 2.65 (d, 2H, CH2-N); 3.93 (s,
2H, CH2-N-thio); 4.28 (s, 1H, NH-iBu); 4.45 (s, 1H,
NH-thio); 6.63 (d, 1H, J = 3.60 Hz, thio ); 6.75 (t,1H,
J = 4.45 Hz, thio); 6.95 (d, 1H, J = 4.45 Hz, thio).
MS (NOBA, FAB > 0): 627 [M + H]+. Anal. calcd for
C9H16N2O2S2: C, 43.52%; H, 6.49; S, 25.82%; found:
C, 43.77%; H, 6.58%; S, 25.53%.
N-(pyridin-4-yl methyl)-N’-(isobutyl)sulfamide 6
Scarcely green powder. Yield: 31%. M.p.:
145°C. TLC: Rf = 0.63 (AcOEt / n-Hexane: 6/4). 1H
NMR (400 MHz, CDCl3, d, ppm): 1.06 (d, 6H, 2CH3);
2.00 (m, 1H, CH(CH3)2); 2.65 (d, 2H, CH2-N); 3.96
(d, 2H, J = 4.66 Hz, CH2-pyr); 4.28 (s, 1H, NH-iBu);
4.50 (s, 1H, NH-pyr) 7.45 (d, 2H, J = 4.65 Hz, pyr);
8.72 (d, 2H, J = 4.68 Hz, pyr). MS (NOBA, FAB > 0):
627 [M + H]+.Anal.calcd for C10H17N3O2S:C, 49.36%;
H, 7.04;S, 13.17%;found: C, 49.51%;H, 7..15%;S,
13.22%.
N-(pyridin-4-yl methyl)-N’-(tert-butyl)
sulfamide 4
Scarcely green powder. Yield: 30%. M.p.:
147°C. TLC: Rf = 0.61 (AcOEt / n-Hexane: 6/4). 1H
NMR (400 MHz, CDCl3, d, ppm): 1.40 (s, 9H, tBu);
3.96 (d, 2H, J = 4.66 Hz, CH2 -pyr); 4.30 (s, 1H,
NH-tBu); 4.50 (s, 1H, NH-pyr) 7.45 (d, 2H, J = 4.65
Hz, pyr); 8.72 (d, 2H, J = 4.68 Hz, pyr). MS (NOBA,
FAB > 0): 627 [M + H]+. Anal. calcd for C10H17N3O2S:
C, 49.36%; H, 7.04; S, 13.17%; found: C, 49.60%;
H, 7.17%; S, 13.25%.
N-(benzyl)-N’-(tert-butyl)sulfamide 7
White powder. Yield: 21%. M.p.: 136°C.
TLC: Rf = 0.70 (AcOEt / n-Hexane: 6/4). 1H NMR
(400 MHz, CDCl3, d, ppm): 1.40 (s, 9H, tBu); 4.15
(d, 2H, J = 5.99 Hz, CH2 -Ph); 4.30 (s, 1H, NH-tBu);
4.47 (s, 1H, NH-Bn); 7.30 (m, 5H, ArH). MS (NOBA,
FAB > 0): 627 [M + H]+. Anal. calcd for C11H18N2O2S:
C, 54.51%; H, 7.48; S, 13.23%; found: C, 54.67%;
H, 7.59%; S, 13.35%.
N-(pyridin-4-yl methyl)-N’-(isopentyl)
N-(benzyl)-N’-(isopentyl)sulfamide 8
sulfamide 5
White powder. Yield: 24%. M.p.: 130°C.
Scarcely green powder. Yield: 33%. M.p.:
142°C. TLC: Rf = 0.66 (AcOEt / n-Hexane: 6/4). 1H
NMR (400 MHz, CDCl3, d, ppm): 1.10 (d, 6H, 2CH3);
1.60 (m, 2H, CH2); 1.90 (m, 1H, CH-(CH3)2); 2.75
(t, 2H, CH2-N); 3.96 (d, 2H, J = 4.66 Hz, CH2 -pyr);
4.26 (s, 1H, NH-isopro); 4.50 (s, 1H, NH-pyr) 7.45
(d, 2H, J = 4.65 Hz, pyr); 8.72 (d, 2H, J = 4.68 Hz,
pyr). MS (NOBA, FAB 0): 627 [M + H]+. Anal. calcd
TLC: Rf = 0.75 (AcOEt / n-Hexane: 6/4). 1H NMR
(400 MHz, CDCl3, d, ppm): 1.10 (d, 6H, 2CH3); 1.60
(m, 2H, CH2); 1.90 (m, 1H, CH-(CH3)2); 2.75 (t, 2H,
CH2-N); 4.15 (d, 2H, J = 5.99 Hz, CH2 -Ph); 4.26 (s,
1H, NH-isopro); 4.47 (s, 1H, NH-Bn); 7.30 (m, 5H,
ArH) .MS (NOBA, FAB > 0):627 [M + H]+.Anal.calcd
for C12H20N2O2S: C, 56.22%; H, 7.86; S, 12.50%;
found: C, 56.33%; H, 8.02%; S, 12.43%.
H
N
H
N
H
N
O
SO2Cl2
O
O
NH2
NH2
R2
S
R2
R1
S
R2
R1
S
R1
R2
R1
N
n-Hexane
N
N
O
O
O
H
H
H
1-9
R2 = tert-butyl
R2 = isopentyl
R2 = isobutyl
R2 = tert-butyl
R2 = isopentyl
R2 = isobutyl
R2 = tert-butyl
R2 = isopentyl
R2 = isobutyl
1: R1 = thiophen-2-yl methyl
2: R1 = thiophen-2-yl methyl
3: R1 = thiophen-2-yl methyl
4: R1 = pyridin-4-yl methyl
5: R1 = pyridin-4-yl methyl
6: R1 = pyridin-4-yl methyl
7: R1 = benzyl
R1 = thiophen-2-yl methyl, pyridin-4-yl methyl, benzyl
R2 = tert-butyl, isopentyl, isobutyl
8: R1 = benzyl
9: R1 = benzyl
Scheme 1: Synthetic Route For The Preparation Of Dissymmetric Sulfamides Derivatives 1-9