Thiourea → HCID 178472878, compound

HRID 1194887Notes

Reaction equation

HRID 1194887 reaction equation
Br[CH2:2][C:3](=O)/[C:4](=[N:10]/[O:11][C@H:12]1[CH2:17][CH2:16][C@H:15]([CH3:18])[CH2:14][CH2:13]1)/[C:5]([O:7][CH2:8][CH3:9])=[O:6].[NH2:20][C:21]([NH2:23])=[S:22]>>[NH2:23][C:21]1[S:22][CH:2]=[C:3](/[C:4](=[N:10]/[O:11][C@H:12]2[CH2:17][CH2:16][C@H:15]([CH3:18])[CH2:14][CH2:13]2)/[C:5]([O:7][CH2:8][CH3:9])=[O:6])[N:20]=1

Participants

3

Reactant 2

HCID 2723790ThioureaHCID 178472881HCID 178472881, compound

Product 1

HCID 178472878HCID 178472878, compoundYield 58%

Procedure

Ethyl 4-bromo-(Z)-2-(trans-4-methylcyclohexyloxyimino)-3-oxobutyrate (1.46 g) was treated with thiourea as described in Example 4d. Crystallisation from cyclohexane gave the title compound as a cream solid (0.80 g, 58%), m.p. 133°-5° C. [Found: M+, 311.1300, C14H21N3O3S requires M, 311.13O3 ]. νmax (KBr) 3447, 3119, 2940, 1723, 1616, 1538 cm-1, δH (CDCl3) 0.89 (3H, d), 0.98 (2H, m), 1.36 (6H, t+m), 1.72 (2H, m), 2.11 (2H, m), 4.16 (1H, m), 4.39 (2H, q), 5.44 (2H, s, exch. D2O) 6.68 (1H, s).

Workup

  1. customCrystallisation from cyclohexane

Sources & evidence

ORD record
ord-d5a6dab8d186434cbe7cbaa7c9d25f36
Source dataset
uspto-grants-1989_03
Patent number
US04816452

Reaction notes

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