Phosphorus oxychloride → 2,4-Dichloro-3,5-dinitrobenzonitrile

Reaction equation

[Cl:1][C:2]1[C:10]([N+:11]([O-:13])=[O:12])=[C:9]([Cl:14])[C:8]([N+:15]([O-:17])=[O:16])=[CH:7][C:3]=1[C:4]([NH2:6])=O.P(Cl)(Cl)(Cl)=O>>[Cl:1][C:2]1[C:10]([N+:11]([O-:13])=[O:12])=[C:9]([Cl:14])[C:8]([N+:15]([O-:17])=[O:16])=[CH:7][C:3]=1[C:4]#[N:6]

Participants

Reactant 2

HCID 24813Phosphorus oxychloride

HCID 964252,4-Dichloro-3,5-dinitrobenzamide

Product 1

HCID 987512,4-Dichloro-3,5-dinitrobenzonitrile

Procedure

A mixture of 66.0 gm. (0.235 mole) of 2,4-dichloro-3,5-dinitrobenzamide and 140 ml. of phosphorus oxychloride is heated at reflux for one hour. The solution is cooled to room temperature. The excess phosphorus oxychloride is distilled off in vacuo. The solid residue is triturated with ice-water and filtered. There is obtained 54.0 g. (88%) of a tan solid melting at 139°-141°.

Workup

additionA mixture of 66.0 gm
temperatureat reflux for one hour
distillationThe excess phosphorus oxychloride is distilled off in vacuo
customThe solid residue is triturated with ice-water
filtrationfiltered
customThere is obtained 54.0 g

Sources & evidence

ORD record: ord-87b4173c935e4915aae7b0d1d29b4574
Source dataset: uspto-grants-1979_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04169153

Reaction notes

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