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 1 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 1 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-da7d4a4d6d6945c4bb8a02c79f6b40e9
Source dataset: uspto-grants-1978_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04091011

Reaction notes

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