Benzoyl isothiocyanate → N-{7-chloro-[1,3]thiazolo[5,4-d]pyrimidin-2-yl}benzamide
Reaction equation
[NH2:1][C:2]1[C:3]([Cl:9])=[N:4][CH:5]=[N:6][C:7]=1Cl.[C:10]([N:18]=[C:19]=[S:20])(=[O:17])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1>CC(C)=O>[Cl:9][C:3]1[C:2]2[N:1]=[C:19]([NH:18][C:10](=[O:17])[C:11]3[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=3)[S:20][C:7]=2[N:6]=[CH:5][N:4]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 25 °C
Procedure
A mixture of 5-amino-4,6-dichloro-pyrimidine (5.0 g, 30.49 mmol) in acetone (30 mL) at 25° C. was treated with benzoyl isothiocyanate (5.5 g, 33.54 mmol). The mixture was stirred at reflux for 6 h and then was cooled to 25° C. The resulting solids were collected by filtration, washed with acetone and petroleum ether and dried in vacuo to afford N-(7-chloro-thiazolo[5,4-d]pyrimidin-2-yl)-benzamide (7.87 g, 79%) as an off-white solid. The NMR spectrum obtained on the sample is compatible with its structure.