Thiourea → ethyl (2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-cyclooctyloxyiminoacetate
Reaction equation
Br[CH2:2][C:3](=O)/[C:4](=[N:10]/[O:11][CH:12]1[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1)/[C:5]([O:7][CH2:8][CH3:9])=[O:6].[NH2:21][C:22]([NH2:24])=[S:23]>>[NH2:24][C:22]1[S:23][CH:2]=[C:3](/[C:4](=[N:10]/[O:11][CH:12]2[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]2)/[C:5]([O:7][CH2:8][CH3:9])=[O:6])[N:21]=1Participants
3
Procedure
Ethyl 4-bromo-(Z)-2-(cyclooctyloxyimino)-3-oxobutyrate (2.8 g) was treated with thiourea as described in Example 4d. Crystallisation from cyclohexane gave the title compound as colourless needles (1.9 g, 72%), m.p. 117°-8° C. [Found, C: 55.66, H: 7.16, N: 12.45. C15H23N3O3S requires C: 55.36, H: 7.12, N: 12.91%]. νmax (KBr) 3428, 2926, 1718, 1610, 1541 cm-1 : δH (CDCl3) 1.35 (3H, t) 1.4-2.0 (14H, m), 4.36 (3H, q+m) 5.65 (2H, br s, exch D2O), 6.66 (1H, s).
Workup
- customCrystallisation from cyclohexane