Benzoyl chloride → 2-Benzamido-N,4-dibenzylthiazole-5-carboxamide

HRID 45387Notes

Reaction equation

[C:1](Cl)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:10][C:11]1[S:12][C:13]([C:23]([NH:25][CH2:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)=[O:24])=[C:14]([CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[N:15]=1>>[C:1]([NH:10][C:11]1[S:12][C:13]([C:23]([NH:25][CH2:26][C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=2)=[O:24])=[C:14]([CH2:16][C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)[N:15]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Reactant 2

HCID 7412Benzoyl chloride

HCID 866425132-Amino-4-benzylthiazole-5-carboxylic Acid Benzylamide

Product 1

HCID 593696382-Benzamido-N,4-dibenzylthiazole-5-carboxamideYield 54%

Procedure

Following the procedure as described in Example 16, making variations only as required to use benzoyl chloride in place of hydrocinnamoyl chloride to react with 2-amino-N,4-dibenzylthiazole-5-carboxamide, the title compound was obtained in 54% yield; 1H NMR (CDCl3, 400 MHz) δ 7.92 (d, J=7.1 Hz, 2H), 7.63 (t, J=7.6 Hz, 1H), 7.52 (t, J=8.1 Hz, 2H), 7.40-7.15 (m, 10H), 4.58 (d, J=5.6 Hz, 2H), 4.41 (s, 2H); MS (ES+) m/z 428 (M+1).

Sources & evidence

ORD record: ord-5cf6499283fd4c9ebbd1cdaba65fe4be
Source dataset: uspto-grants-2013_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08541457B2

Reaction notes

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