[N+:1]([C:4]1[CH:10]=[CH:9][C:7]([NH2:8])=[CH:6][CH:5]=1)([O-:3])=[O:2].[P:11](Cl)([Cl:14])([Cl:13])=[O:12]>>[N+:1]([C:4]1[CH:10]=[CH:9][C:7]([NH:8][P:11]([Cl:14])([Cl:13])=[O:12])=[CH:6][CH:5]=1)([O-:3])=[O:2]To 300 ml of phosphorous oxychloride was carefully added 69 g (0.5 m) of 4-nitroaniline. The mixture was heated at reflux for 3 hours, then chilled to 10°. The crude product was collected by filtration, washed with ether and air-dried to give 93.6 g, m.p. 156.5°-157.5°.
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