4-Nitroaniline → N-(4-Nitrophenyl)phosphoramidic dichloride

Reaction equation

[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]

Participants

Reactant 2

HCID 74754-Nitroaniline

HCID 24813Phosphorus oxychloride

Product 1

HCID 12843950N-(4-Nitrophenyl)phosphoramidic dichloride

Procedure

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°.

Workup

temperatureThe mixture was heated
temperatureat reflux for 3 hours
temperaturechilled to 10°
filtrationThe crude product was collected by filtration
washwashed with ether
customair-dried
customto give 93.6 g, m.p. 156.5°-157.5°

Sources & evidence

ORD record: ord-7f4aa35eb03f4ab9957b2d92602c5651
Source dataset: uspto-grants-1980_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04242325

Reaction notes

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