Thiourea → HCID 178472884, compound

HRID 1194924Notes

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]([Cl: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]([Cl:18])[CH2:14][CH2:13]2)/[C:5]([O:7][CH2:8][CH3:9])=[O:6])[N:20]=1

Participants

Reactant 2

HCID 2723790Thiourea

HCID 178472887HCID 178472887, compound

Product 1

HCID 178472884HCID 178472884, compound

Procedure

Ethyl 4-bromo- (Z)-2-(trans-4-chlorocyclohexyloxyimino)-3-oxobutyrate (730 mg) was treated with thiourea as described in Example 4d, to give the title compound (579 mg, 85%) m.p. 155° C. (ethyl acetate-hexane) (Found: C, 47.05; H, 5.02; N, 12.75; Cl, 10.8; S, 9.73. C13H18N3CLO3S requires C,47.1; H, 5.4; N, 12.7; Cl, 10.7; S, 9.7%). νmax (Nujol) 3450, 3430, 3250, 3125, 1720, 1615, 1610, and 1540 cm-1, νH (CDCl3), 1.36 (3H, t, J 7.1 Hz), 1.73 (4H, m), 2.13 (4H, m), 4.18 (1H, m), 4.39 (2H, q, J 7.1 Hz), latter signal obscures single hydrogen multiplet, 5.5 (2H, s, exch. D2O), and 6.71 (1H, s).

Sources & evidence

ORD record: ord-a98d3b3f797e46b5ac7c746013a7548c
Source dataset: uspto-grants-1989_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04816452

Reaction notes

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