N-Benzyl-2-imino-4-methyl-2,3-dihydro-1,3-thiazole-5-carboximidic acid → HCID 59369668, compound

HRID 45359Notes

Reaction equation

HRID 45359 reaction equation
[CH3:1][S:2]([C:5]1[CH:6]=[C:7]([CH:11]=[CH:12][CH:13]=1)[C:8](Cl)=[O:9])(=[O:4])=[O:3].[CH2:14]([NH:21][C:22]([C:24]1[S:28][C:27]([NH2:29])=[N:26][C:25]=1[CH3:30])=[O:23])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>>[CH2:14]([NH:21][C:22]([C:24]1[S:28][C:27]([NH:29][C:8](=[O:9])[C:7]2[CH:11]=[CH:12][CH:13]=[C:5]([S:2]([CH3:1])(=[O:4])=[O:3])[CH:6]=2)=[N:26][C:25]=1[CH3:30])=[O:23])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

3

Reactant 2

HCID 210824N-Benzyl-2-imino-4-methyl-2,3-dihydro-1,3-thiazole-5-carboximidic acidHCID 221378393-(Methanesulfonyl)benzoyl chloride

Product 1

HCID 59369668HCID 59369668, compoundYield 15%

Procedure

Following the procedure as described in Example 2, making variations only as required to use 3-methanesulfonylbenzoyl 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 15% yield; m.p. 111-113° C.; 1H NMR (CD3OD, 300 MHz) δ 8.55 (t, J=5.8 Hz, 1H), 8.09 (dd, J=1.2, 7.6 Hz, 1H), 7.36-7.19 (m, 2H), 7.68 (dd, J=1.2, 7.6 Hz, 1H), 7.27 (m, 5H), 4.50 (d, J=1.9 Hz, 2H), 3.33 (s, 3H), 2.52 (s, 3H); MS (ES+) m/z 430.1 (M+1).

Sources & evidence

ORD record
ord-a62eee1ce8564e0a98b071d6c4f81331
Source dataset
uspto-grants-2013_09
Patent number
US08541457B2

Reaction notes

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