Ethyl bromopyruvate → (2-((4-Chlorophenyl)amino)thiazol-4-yl)(3,4,5-trimethoxyphenyl)methanone

HRID 70050Notes

Reaction equation

HRID 70050 reaction equation
[C:1]1([NH:7][C:8]2[S:9][CH:10]=[C:11]([C:13]([C:15]3[CH:20]=[C:19]([O:21][CH3:22])[C:18]([O:23][CH3:24])=[C:17]([O:25][CH3:26])[CH:16]=3)=[O:14])[N:12]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Cl:27]C1C=CC(NC(N)=S)=CC=1.BrCC(=O)C(OCC)=O>>[Cl:27][C:4]1[CH:5]=[CH:6][C:1]([NH:7][C:8]2[S:9][CH:10]=[C:11]([C:13]([C:15]3[CH:20]=[C:19]([O:21][CH3:22])[C:18]([O:23][CH3:24])=[C:17]([O:25][CH3:26])[CH:16]=3)=[O:14])[N:12]=2)=[CH:2][CH:3]=1

Participants

4

Reactant 3

HCID 66144Ethyl bromopyruvateHCID 735843Thourea, (4-chlorophenyl)- (9CI)HCID 53361717HCID 53361717, compound

Product 1

HCID 56846908(2-((4-Chlorophenyl)amino)thiazol-4-yl)(3,4,5-trimethoxyphenyl)methanone

Procedure

(2-((4-Chlorophenyl)amino)thiazol-4-yl)(3,4,5-trimethoxyphenyl)methanone (5d) was prepared using the same method as used for 5a from 1-(4-chlorophenyl)thiourea and ethyl bromopyruvate. Melting point: 165-166° C. 1H NMR (500 MHz, CDCl3) δ 7.60 (s, br, 1H), 7.56 (s, 1H), 7.47 (s, 2H), 7.38 (d, 2H), 7.31 (d, 2H), 3.94 (s, 3H), 3.89 (s, 6H). MS: 402.9 (M−1)−; 427.0 (M+Na)+.

Sources & evidence

ORD record
ord-7fb45943432944fc9a8a4ed596afc504
Source dataset
uspto-grants-2014_09
Patent number
US08822513B2

Reaction notes

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