4-Toluenesulfonyl chloride → 4-Methyl-2-(toluene-4-sulfonylamino)thiazole-5-carboxylic Acid Benzylamide

HRID 45366Notes

Reaction equation

HRID 45366 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([S:8](Cl)(=[O:10])=[O:9])=[CH:4][CH:3]=1.[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][S:8]([C:5]2[CH:6]=[CH:7][C:2]([CH3:1])=[CH:3][CH:4]=2)(=[O:10])=[O:9])=[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 73974-Toluenesulfonyl chlorideHCID 210824N-Benzyl-2-imino-4-methyl-2,3-dihydro-1,3-thiazole-5-carboximidic acid

Product 1

HCID 169448144-Methyl-2-(toluene-4-sulfonylamino)thiazole-5-carboxylic Acid BenzylamideYield 43%

Procedure

Following the procedure as described in Example 2, making variations only as required to use 4-methylbenzenesulfonyl 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 43% yield; m.p. 242-245° C.; 1H NMR (DMSO-d6, 300 MHz) δ 12.89 (s, br, 1H), 8.58 (s, br, 1H), 7.66 (d, J=8.2 Hz, 2H), 7.33-7.17 (m, 7H), 4.32 (d, J=5.8 Hz, 2H), 2.32 (s, 3H), 2.31 (s, 3H); 13C NMR (DMSO-d6, 75 MHz) δ 166.2, 160.6, 143.0, 139.7, 139.6, 139.5, 129.9, 128.7, 127.8, 127.3, 126.2, 111.7, 43.1, 21.4, 13.6; MS (ES+) m/z 402.4 (M+1).

Sources & evidence

ORD record
ord-34855ba63c2741f185232a73d2254ea5
Source dataset
uspto-grants-2013_09
Patent number
US08541457B2

Reaction notes

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