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

HRID 1863493Notes

Reaction equation

HRID 1863493 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

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 96425Benzamide, 2,4-dichloro-3,5-dinitro-

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

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

Sources & evidence

ORD record
ord-87b4173c935e4915aae7b0d1d29b4574
Source dataset
uspto-grants-1979_09
Patent number
US04169153

Reaction notes

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