Benzoyl chloride, 3-nitro- → 2'-Cyano-3,4'-dinitrobenzanilide

HRID 236990

Reaction equation

HRID 236990 reaction equation
[NH2:1][C:2]1[CH:9]=[CH:8][C:7]([N+:10]([O-:12])=[O:11])=[CH:6][C:3]=1[C:4]#[N:5].[N+:13]([C:16]1[CH:17]=[C:18]([CH:22]=[CH:23][CH:24]=1)[C:19](Cl)=[O:20])([O-:15])=[O:14]>N1C=CC=CC=1>[C:4]([C:3]1[CH:6]=[C:7]([N+:10]([O-:12])=[O:11])[CH:8]=[CH:9][C:2]=1[NH:1][C:19](=[O:20])[C:18]1[CH:22]=[CH:23][CH:24]=[C:16]([N+:13]([O-:15])=[O:14])[CH:17]=1)#[N:5]

Participants

4

Reactant 2

HCID 8495Benzoyl chloride, 3-nitro-HCID 285322-Amino-5-nitrobenzonitrile

Product 1

HCID 213150352'-Cyano-3,4'-dinitrobenzanilide

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of 8.16 gm. (0.05 mole) of 2-amino-5-nitrobenzonitrile and 9.28 gm. (0.05 mole) of m-nitro benzoyl chloride in 50 ml. of dry pyridine is refluxed for three hours. The pyridine is removed by distillation in vacuo and the solid residue triturated with water. There is obtained 15.3 gm. (95%) of a yellow solid that melts at 203°-205°. Recrystallization from aqueous ethanol (2:1) gives material melting at 205°-206°.

Workup

  1. customThe pyridine is removed by distillation in vacuo
  2. customthe solid residue triturated with water
  3. customThere is obtained 15.3 gm
  4. customRecrystallization from aqueous ethanol (2:1)

Sources & evidence

ORD record
ord-03879b62f16a416ea71efffba1818eef
Source dataset
uspto-grants-1979_06
Patent number
US04159341

Linked notes

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