N,N-Dimethylaniline → HCID 88627012, compound

HRID 1194911Notes

Reaction equation

HRID 1194911 reaction equation
Br[CH2:2][C:3](=O)/[C:4](=[N:10]/[O:11][C@@H:12]1[CH2:17][CH2:16][CH2:15][CH2:14][C@H:13]1[O:18][CH3:19])/[C:5]([O:7][CH2:8][CH3:9])=[O:6].[NH2:21][C:22]([NH2:24])=[S:23].CN(C)C1C=CC=CC=1>>[NH2:24][C:22]1[S:23][CH:2]=[C:3](/[C:4](=[N:10]/[O:11][C@@H:12]2[CH2:17][CH2:16][CH2:15][CH2:14][C@H:13]2[O:18][CH3:19])/[C:5]([O:7][CH2:8][CH3:9])=[O:6])[N:21]=1

Participants

4

Reactant 3

HCID 949N,N-DimethylanilineHCID 2723790ThioureaHCID 88627132HCID 88627132, compound

Product 1

HCID 88627012HCID 88627012, compound

Procedure

Ethyl 4-bromo-(Z)-2-(trans-2-methoxycyclohexyloxyimino)-3-oxobutyrate was treated with thiourea (0.79 g) and N,N-dimethylaniline (1.318 ml) as described in Example 4d to give the title compound as an orange gum (1.78 g) after silica gel chromatography. νmax (CH2Cl2) 3460, 3370, 3250, 3100, 1730, 1605, and 1530 cm-1 ; δH (CDCl3) inter alia 1.10-1.20 (11H, m), 3.32 (1H, m), 3.43 (3H, s), 4.00-4.50 (3H, m), 6.55 (2H, br. s), and 6.66 (1H, s). [Mass spectrum: EI M+ (327)].

Sources & evidence

ORD record
ord-54185a45ceaa4eba86ef02ddf7ddedc1
Source dataset
uspto-grants-1989_03
Patent number
US04816452

Reaction notes

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