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

HRID 839438Notes

Reaction equation

HRID 839438 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-a86df7a1b67c46248581de07d0973b98
Source dataset
uspto-grants-1978_06
Patent number
US04095028

Reaction notes

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