2-Chlorobenzoyl chloride → 2-(2-Chlorobenzoylamino)-4-methylthiazole-5-carboxylic Acid Benzylamide

HRID 45343Notes

Reaction equation

HRID 45343 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4](Cl)=[O:5].[CH2:11]([NH:18][C:19]([C:21]1[S:25][C:24]([NH2:26])=[N:23][C:22]=1[CH3:27])=[O:20])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>>[CH2:11]([NH:18][C:19]([C:21]1[S:25][C:24]([NH:26][C:4](=[O:5])[C:3]2[CH:7]=[CH:8][CH:9]=[CH:10][C:2]=2[Cl:1])=[N:23][C:22]=1[CH3:27])=[O:20])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

3

Reactant 2

HCID 691102-Chlorobenzoyl chlorideHCID 210824N-Benzyl-2-imino-4-methyl-2,3-dihydro-1,3-thiazole-5-carboximidic acid

Product 1

HCID 14682622-(2-Chlorobenzoylamino)-4-methylthiazole-5-carboxylic Acid BenzylamideYield 13%

Procedure

Following the procedure as described in Example 2, making variations only as required to use 2-chlorobenzoyl chloride in place of benzoyl chloride to react with 2-amino-4-methylthiazole-5-carboxylic acid benzylamide, the title compound was obtained as a white solid in 13% yield; 1H NMR (CDCl3, 300 MHz) δ 7.78 (d, J=7.8 Hz, 1H), 7.46-7.27 (m, 8H), 5.95 (s, 1H), 4.57 (d, J=4.6 Hz, 2H), 2.33 (s, 3H); MS (ES+) m/z 386.1 (M+1).

Sources & evidence

ORD record
ord-9eadd7900c974d6b91e4bf8effd7db83
Source dataset
uspto-grants-2013_09
Patent number
US08541457B2

Reaction notes

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