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

HRID 263053

Reaction equation

HRID 263053 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-02827a8b5306486fb644ed90a7cf4913
Source dataset
uspto-grants-1979_05
Patent number
US04156012

Linked notes

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