N,N-Dimethylaniline → HCID 88627764, compound

HRID 1194935Notes

Reaction equation

HRID 1194935 reaction equation
Br[CH2:2][C:3](=O)/[C:4](=[N:10]/[O:11][C@H:12]1[CH2:17][CH2:16][CH2:15][C@@H:14]([CH3:18])[CH2:13]1)/[C:5]([O:7][CH2:8][CH3:9])=[O:6].CN(C)C1C=CC=CC=1.[NH2:29][C:30]([NH2:32])=[S:31].C(OCC)(=O)C.CCCCCC>C(O)C.C(Cl)(Cl)Cl>[NH2:32][C:30]1[S:31][CH:2]=[C:3](/[C:4](=[N:10]/[O:11][C@H:12]2[CH2:17][CH2:16][CH2:15][C@@H:14]([CH3:18])[CH2:13]2)/[C:5]([O:7][CH2:8][CH3:9])=[O:6])[N:29]=1

Participants

7

Reactant 4

HCID 949N,N-DimethylanilineHCID 2723790ThioureaHCID 21226206Ethyl acetate hexaneHCID 154041577HCID 154041577, compound

Product 1

HCID 88627764HCID 88627764, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6212ChloroformSolvent

Procedure

Ethyl 4-bromo-(Z)-2-(cis 3-methylcyclohexyl)oxyimino-3-oxobutyrate (7.2 mmol) was treated with N,N-dimethylaniline (0.91 ml; 7.2 mmol) and thiourea (0.55 g, 7.2 mmol) in ethanol as described in Example 4d, except that the reaction was worked up after 2 h. The title compound was obtained as a white crystalline solid (1.78 g; 79%) m.p. 91°-93° C. (ethyl acetate/hexane), (Found: C, 54.29; H, 6.88; N, 13.57. C14H21N3O3S requires C, 54; H, 6.79; N, 13.49%), νmax (CHCl3) 3480, 3400, 1730, and 1610 cm-1 ; δH (CDCl3) 0.64-1.1 (2H, m, partially obscured by d, δ 0.92), 0.92 (3H, d, J 5.5 Hz), 1.1-1.55 (3H, m, partially obscured by t, δ 1.36), 1.36 (3H, t, J 7.1 Hz), 1.55-1.70 (1H, m) 1.70-1.86 (1H, m), 2.03-2.25 (2H, m), 4.20 (1H, tt, J 11.1 and 4.3 Hz), 4.39 (2H, q, J 7.1 Hz), 5.31 (2H, broad s), and 6.7 (1H, s).

Sources & evidence

ORD record
ord-508a622ce9164c52969fbc6272d9af67
Source dataset
uspto-grants-1989_03
Patent number
US04816452

Reaction notes

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