3,5-Dichlorobenzoyl chloride → HCID 59369659, compound

HRID 45348

Reaction equation

HRID 45348 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([Cl:11])[CH:10]=1)[C:5](Cl)=[O:6].[CH2:12]([NH:19][C:20]([C:22]1[S:26][C:25]([NH2:27])=[N:24][C:23]=1[CH3:28])=[O:21])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>>[CH2:12]([NH:19][C:20]([C:22]1[S:26][C:25]([NH:27][C:5](=[O:6])[C:4]2[CH:3]=[C:2]([Cl:1])[CH:10]=[C:9]([Cl:11])[CH:8]=2)=[N:24][C:23]=1[CH3:28])=[O:21])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

3

Reactant 2

HCID 761913,5-Dichlorobenzoyl chlorideHCID 210824N-Benzyl-2-imino-4-methyl-2,3-dihydro-1,3-thiazole-5-carboximidic acid

Product 1

HCID 59369659HCID 59369659, compoundYield 34%

Procedure

Following the procedure as described in Example 2, making variations only as required to use 3,5-dichlorobenzoyl 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 34% yield; m.p. 104-105° C.; 1H NMR (CDCl3, 300 MHz) δ 7.69 (d, J=1.9 Hz, 2H), 7.52 (t, J=1.9, 1H), 7.35-7.31 (m, 5H), 6.04 (t, J=5.6 Hz, 1H), 4.59 (d, J=5.6 Hz, 2H), 2.44 (s, 3H); MS (ES+) m/z 420 (M+1).

Sources & evidence

ORD record
ord-47fc79354fe046369fd5ddec5e9ceb83
Source dataset
uspto-grants-2013_09
Patent number
US08541457B2

Linked notes

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