Benzylamine → 2-Benzoylaminothiazole-5-carboxylic Acid Benzylamide
Reaction equation
CO[C:3]([C:5]1[S:9][C:8]([NH:10][C:11](=[O:18])[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[N:7][CH:6]=1)=[O:4].[C-]#N.[Na+].[CH2:22]([NH2:29])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>>[CH2:22]([NH:29][C:3]([C:5]1[S:9][C:8]([NH:10][C:11](=[O:18])[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)=[N:7][CH:6]=1)=[O:4])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1Participants
Conditions
- Temperature
- 80 °C
Procedure
A mixture of 2-benzoylaminothiazole-5-carboxylic acid methyl ester (0.40 g, 1.52 mmol), sodium cyanide (0.19 g, 3.79 mmol) and benzylamine (4 mL) was stirred at 80° C. for 70 h. The mixture was filtered, washed with ethyl ether, and the filtrate was concentrated in vacuo. The residue was dissolved in a mixture of methanol and tetrahydrofuran and aqueous lithium hydroxide solution (0.24 g in 6 mL water) was added. The mixture was stirred at 50° C. for 4 d. The organic solvents were removed in vacuo. The solid obtained was collected by filtration, washed with water, methanol and dried. The title compound was obtained as a white solid in 5% yield (0.005 g); 1H NMR (DMSO-d6, 300 MHz) δ 8.93 (s, 1H), 8.20-8.03 (m, 3H), 7.62-7.41 (m, 3H), 7.39-7.14 (m, 6H), 4.43 (d, J=3.9 Hz, 2H); MS (ES+) m/z 338.5 (M+1).
Workup
- filtrationThe mixture was filtered
- washwashed with ethyl ether
- concentrationthe filtrate was concentrated in vacuo
- dissolutionThe residue was dissolved in a mixture of methanol and tetrahydrofuran and aqueous lithium hydroxide solution (0.24 g in 6 mL water)
- additionwas added
- stirringThe mixture was stirred at 50° C. for 4 d
- customThe organic solvents were removed in vacuo
- customThe solid obtained
- filtrationwas collected by filtration
- washwashed with water, methanol
- customdried
Sources & evidence
- ORD record
- ord-50877a11e551451893bbe6941683197a
- Source dataset
- uspto-grants-2013_09
- Patent number
- US08541457B2
Reaction notes
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