Phosphorus oxychloride → 2-chloro-3,5-dinitrobenzonitrile

HRID 236935Notes

Reaction equation

HRID 236935 reaction equation
[Cl:1][C:2]1[C:10]([N+:11]([O-:13])=[O:12])=[CH:9][C:8]([N+:14]([O-:16])=[O:15])=[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])=[CH:9][C:8]([N+:14]([O-:16])=[O:15])=[CH:7][C:3]=1[C:4]#[N:6]

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 2356272-chloro-3,5-dinitrobenzamide

Product 1

HCID 42574512-chloro-3,5-dinitrobenzonitrile

Procedure

A mixture of 31.8 gm. (0.129 mole) of 2-chloro-3,5-dinitrobenzamide and 50 ml. of phosphorous oxychloride is heated under reflux for one hour. The excess phosphorous oxychloride is removed by distillation under reduced pressure. To the residue is cautiously added ice water. The light yellow-green solid is removed by filtration and washed with water. There is obtained 28.0 g. (95%) of material melting at 139°-41°.

Workup

  1. additionA mixture of 31.8 gm
  2. temperatureunder reflux for one hour
  3. customThe excess phosphorous oxychloride is removed by distillation under reduced pressure
  4. customThe light yellow-green solid is removed by filtration
  5. washwashed with water
  6. customThere is obtained 28.0 g

Sources & evidence

ORD record
ord-448ea68a55ae4343ab55d2f35901d78c
Source dataset
uspto-grants-1979_06
Patent number
US04159278

Reaction notes

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