4-(Trifluoromethoxy)benzoyl Chloride → 4-Methyl-2-(4-trifluoromethoxybenzoylamino)thiazole-5-carboxylic Acid Benzylamide

HRID 45356Notes

Reaction equation

HRID 45356 reaction equation
[F:1][C:2]([F:14])([F:13])[O:3][C:4]1[CH:12]=[CH:11][C:7]([C:8](Cl)=[O:9])=[CH:6][CH:5]=1.[CH2:15]([NH:22][C:23]([C:25]1[S:29][C:28]([NH2:30])=[N:27][C:26]=1[CH3:31])=[O:24])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>>[CH2:15]([NH:22][C:23]([C:25]1[S:29][C:28]([NH:30][C:8](=[O:9])[C:7]2[CH:11]=[CH:12][C:4]([O:3][C:2]([F:14])([F:13])[F:1])=[CH:5][CH:6]=2)=[N:27][C:26]=1[CH3:31])=[O:24])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

3

Reactant 2

HCID 1421104-(Trifluoromethoxy)benzoyl ChlorideHCID 210824N-Benzyl-2-imino-4-methyl-2,3-dihydro-1,3-thiazole-5-carboximidic acid

Product 1

HCID 866425184-Methyl-2-(4-trifluoromethoxybenzoylamino)thiazole-5-carboxylic Acid BenzylamideYield 20%

Procedure

Following the procedure as described in Example 2, making variations only as required to use 4-trifluoromethoxybenzoyl 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 20% yield; m.p. 168-170° C.; 1H NMR (CDCl3, 300 MHz) δ 7.98 (d, J=8.8 Hz, 2H), 7.41-7.23 (m, 7H), 5.97 (t, J=5.6 Hz, 1H), 4.58 (d, J=5.6 Hz, 2H), 2.49 (s, 3H); MS (ES+) m/z 436.1 (M+1).

Sources & evidence

ORD record
ord-482c5552969843978d173282f62a57c0
Source dataset
uspto-grants-2013_09
Patent number
US08541457B2

Reaction notes

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