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

HRID 1730678Notes

Reaction equation

HRID 1730678 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 1 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 1 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-7adae5d0235e4664aa7c84f035b8157d
Source dataset
uspto-grants-1976_11
Patent number
US03993679

Reaction notes

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