N-Benzyl-2-imino-4-methyl-2,3-dihydro-1,3-thiazole-5-carboximidic acid → HCID 59369666, compound

HRID 45365Notes

Reaction equation

HRID 45365 reaction equation
[CH:1]1([CH2:4][C:5](Cl)=[O:6])[CH2:3][CH2:2]1.[CH2:8]([NH:15][C:16]([C:18]1[S:22][C:21]([NH2:23])=[N:20][C:19]=1[CH3:24])=[O:17])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1>>[CH2:8]([NH:15][C:16]([C:18]1[S:22][C:21]([NH:23][C:5](=[O:6])[CH2:4][CH:1]2[CH2:3][CH2:2]2)=[N:20][C:19]=1[CH3:24])=[O:17])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

3

Reactant 2

HCID 210824N-Benzyl-2-imino-4-methyl-2,3-dihydro-1,3-thiazole-5-carboximidic acidHCID 143262682-Cyclopropylacetyl chloride

Product 1

HCID 59369666HCID 59369666, compoundYield 27%

Procedure

Following the procedure as described in Example 2, making variations only as required to use cyclopropylacetyl 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 27% yield; m.p. 136-139° C.; 1H NMR (CDCl3, 300 MHz) δ 7.34-7.24 (m, 5H), 5.97 (s, 1H), 4.57 (d, J=5.6 Hz, 2H), 2.60 (s, 3H), 2.39 (d, J=7.2 Hz, 2H), 1.05-1.00 (m, 1H), 0.71-0.68 (m, 2H), 0.27 (q, J=4.8 Hz, 2H); MS (ES+) m/z 330.1 (M+1).

Sources & evidence

ORD record
ord-db4b629e190b488e811418315d6274d6
Source dataset
uspto-grants-2013_09
Patent number
US08541457B2

Reaction notes

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