N-Benzyl-2-imino-4-methyl-2,3-dihydro-1,3-thiazole-5-carboximidic acid → HCID 59369651, compound

HRID 45360Notes

Reaction equation

[CH3:1][S:2]([C:5]1[CH:13]=[CH:12][CH:11]=[CH:10][C:6]=1[C:7](Cl)=[O:8])(=[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:7](=[O:8])[C:6]2[CH:10]=[CH:11][CH:12]=[CH:13][C:5]=2[S:2]([CH3:1])(=[O:4])=[O:3])=[N:26][C:25]=1[CH3:30])=[O:23])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

Reactant 2

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

HCID 125767992-(Methylsulfonyl)benzoyl chloride

Product 1

HCID 59369651HCID 59369651, compoundYield 9%

Procedure

Following the procedure as described in Example 2, making variations only as required to use 2-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 9% yield; m.p. 239-242° C.; 1H NMR (DMSO-d6, 300 MHz) δ 8.64 (t, J=5.8 Hz, 1H), 8.59 (s, 1H), 8.35 (d, J=7.8 Hz, 1H), 8.13 (d, J=7.8 Hz, 1H), 7.80 (t, J=7.8 Hz, 1H), 7.33-7.19 (m, 6H), 4.38 (d, J=5.8 Hz, 2H), 3.26 (s, 3H), 2.51 (s, 3H); MS (ES+) m/z 430.1 (M+1).

Sources & evidence

ORD record: ord-6b11e4c8b2e64b37aa844c0c55dd9687
Source dataset: uspto-grants-2013_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08541457B2

Reaction notes

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