following method B. Using path B, method A afforded 248 mg (78%) of 4d and 219 mg
(69%) were obtained following method B. mp 143-145°C. IR (KBr): ν 1714 (C=O), 1228
(C=S) cm-1. 1H-NMR (CDCl3): δ 0.95 (3H, m, CH3), 1.40-1.70 (4H, 2m, 2 x CH2), 3.62 (3H,
s, N(1)-CH3), 3.96 (2H, t, J = 7.52 Hz, N(3)-CH2), 6.00 (2H, s, CH2), 6.48 (1H, s, =CH),
7.48 (2H, s, H-Ar), 7.98 (1H, s, H-Ar). Anal. Calcd for C16H18N2O3S: C, 60.4, H, 5.7; N, 8.8.
Found: C, 60.3; H, 5.9; N, 8.5.
5-((E)-3,4-Methylenedioxybenzylidene)-3-n-hexyl-1-methyl-2-thiohydantoin (4e):
Using path A, method A afforded 301 mg (87%) of 4e and 315 mg (91%) were obtained
following method B. Using path B, method A afforded 277 mg (80%) of 4e and 256 mg
(74%) were obtained following method B. mp 120-122°C. IR (KBr): ν 1713 (C=O), 1232
(C=S) cm-1. 1H-NMR (CDCl3): δ 0.80 (3H, t, J = 7.5 Hz, CH3), 1.25 (6H, m, 3CH2), 1.61 (2H,
m, CH2), 3.55 (3H, s, N(1)-CH3), 3.92 (2H, t, J = 7.5 Hz, N(3)-CH2), 5.98 (2H, s, CH2), 6.35
(1H, s, =CH), 7.35 (2H, 2d, J = 7.3 Hz, H-Ar), 7.94 (1H, s, H-Ar). Anal. Calcd for
C18H22N2O3S: C, 62.4, H, 6.4; N, 8.1. Found: C, 62.3; H, 6.5; N, 8.0.
5-((E)-3,4-Methylenedioxybenzylidene)-3-cyclohexylmethyl-1-methyl-2-thiohydantoin
(4f): Using path A, method A afforded 322 mg (90%) of 4f and 343 mg (96%) were
obtained following method B. Using path B, method A afforded 297 mg (83%) of 4f and
283 mg (79%) were obtained following method B. mp 160-162°C. IR (KBr): ν 1712 (C=O),
1
1228 (C=S) cm-1. H-NMR (CDCl3): δ 1.00-1.24 (6H, m, H-3, H-4, H-5cyclohexane), 1.65 (4H,
m, H-2, H-6cyclohexane), 1.96 (1H, m, H-1cyclohexane), 3.60 (3H, s, N(1)-CH3), 3.78 (2H, d, J =
7.5 Hz, N(3)-CH2), 6.02 (2H, s, CH2), 6.40 (1H, s, =CH), 6.84 (1H, d, J = 8.1 Hz, H-Ar),
7.36 (1H, d, J = 8.1 Hz, H-Ar), 7.98 (1H, s, H-Ar). Anal. Calcd for C19H22N2O3S: C, 63.7, H,
6.2; N, 7.8. Found: C, 63.5; H, 6.5; N, 7.6.
5-((E)-3,4-Methylenedioxybenzylidene)-3-[2-(4-morpholino)ethyl]-1-methyl-2-
thiohydantoin (4g): Using path A, method A afforded 348 mg (86%) of 4g and 372 mg
(92%) were obtained following method B. Using path B, method A afforded 316 mg (78%)
of 4g and 292 mg (72%) were obtained following method B. mp 163-165°C. IR (KBr): ν
1717 (C=O), 1230 (C=S) cm-1. 1H-NMR (CDCl3): δ 2.48 (4H, t, J = 4.5 Hz, H-2’, H-6’), 2.64
(2H, t, J = 6.9 Hz, N-CH2), 3.52 (3H, s, N(1)-CH3), 3.60 (4H, t, J = 4.5 Hz, H-3’, H-5’), 4.00
(2H, t, J = 6.9 Hz, N(3)-CH2), 6.02 (2H, s, CH2), 6.40 (1H, s, =CH), 6.84 (1H, d, J = 8.1 Hz,
H-Ar), 7.36 (1H, d, J = 8.1 Hz, H-Ar), 7.98 (1H, s, H-Ar). Anal. Calcd for C20H26N3O4S: C,
59.4, H, 6.5; N, 10.4. Found: C, 59.3; H, 6.2; N, 10.7.