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

HRID 461212Notes

Reaction equation

HRID 461212 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 3 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-1bf1c090799e4b69a5bd3bccdac28bd3
Source dataset
uspto-grants-1977_12
Patent number
US04061791

Reaction notes

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