Phosgene → 4-(5-Bromo-2-pyrimidinyloxy)-3-chlorophenylisocyanate
Reaction equation
[C:1](Cl)(Cl)=[O:2].[Br:5][C:6]1[CH:7]=[N:8][C:9]([O:12][C:13]2[CH:19]=[CH:18][C:16]([NH2:17])=[CH:15][C:14]=2[Cl:20])=[N:10][CH:11]=1>C(OCC)(=O)C>[Br:5][C:6]1[CH:11]=[N:10][C:9]([O:12][C:13]2[CH:19]=[CH:18][C:16]([N:17]=[C:1]=[O:2])=[CH:15][C:14]=2[Cl:20])=[N:8][CH:7]=1Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
Into a flask, a solution of 0.02 mol of phosgene in 30 ml of ethyl acetate was introduced. To this solution, a solution of 3 g of 4-(5-bromo-2-pyrimidinyloxy)-3-chloroaniline in 10 ml of ethyl acetate was dropwise added at room temperature. The mixture was reacted at room temperature for 3 hours under stirring and further under reflux for one hour. After completion of the reaction, ethyl acetate was distilled off under reduced pressure, and the residue was vacuum-dried to obtain 3.10 g of 4-(5-bromo-2-pyrimidinyloxy)-3-chlorophenylisocyanate having a melting point of from 63 to 68° C. (2) Into a flask, 1.22 g of 4-(5-bromo-2-pyrimidinyloxy)-3-chlorophenylisocyanate obtained in the above step was introduced, and 20 ml of toluene was added thereto. Further, 0.62 g of 2-nitrobenzamide was added under stirring. The mixture was reacted under reflux for 4 hours. After completion of the reaction, 5 ml of methanol was added to the reaction product, and the mixture was cooled. The precipitated crystals were collected by filtration to obtain 0.79 g of the desired product.
Workup
- customThe mixture was reacted at room temperature for 3 hours
- temperaturefurther under reflux for one hour
- distillationwas distilled off under reduced pressure
- customthe residue was vacuum-dried
Sources & evidence
- ORD record
- ord-7ff718f3b7e94c629eff1d63f4573f1b
- Source dataset
- uspto-grants-1988_02
- Patent number
- US04727077
Reaction notes
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