Sodium Hydroxide → N'-(2,6-dichloro-4-trifluoromethylphenyl)-4-cyanobenzohydrazide

HRID 2228841Notes

Reaction equation

HRID 2228841 reaction equation
[C:1]([C:3]1[CH:11]=[CH:10][C:6]([C:7](Cl)=[O:8])=[CH:5][CH:4]=1)#[N:2].[Cl:12][C:13]1[CH:18]=[C:17]([C:19]([F:22])([F:21])[F:20])[CH:16]=[C:15]([Cl:23])[C:14]=1[NH:24][NH2:25].[OH-].[Na+]>C(Cl)Cl>[Cl:12][C:13]1[CH:18]=[C:17]([C:19]([F:21])([F:20])[F:22])[CH:16]=[C:15]([Cl:23])[C:14]=1[NH:24][NH:25][C:7](=[O:8])[C:6]1[CH:10]=[CH:11][C:3]([C:1]#[N:2])=[CH:4][CH:5]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 801724-Cyanobenzoyl chlorideHCID 688223[2,6-Dichloro-4-(trifluoromethyl)phenyl]hydrazine

Product 1

HCID 18471605N'-(2,6-dichloro-4-trifluoromethylphenyl)-4-cyanobenzohydrazide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

A solution of 14.2 g of 4-cyanobenzoyl chloride in 100 ml of methylene chloride is added dropwise with stirring at from 10 to 15° in the course of approximately 30 minutes to 20 g of 2,6-dichloro-4-trifluoromethylphenylhydrazine in 250 ml of dichloromethane, and the mixture is stirred for a further 16 hours. 36 ml of aqueous sodium hydroxide solution (10%) is then run in with vigorous stirring. 100 ml of methylene chloride are added, the organic phase is washed three times using in each case 100 ml of water and dried over sodium sulfate, and the solvent is removed on a rotary evaporator. After the residue has been recrystallized from toluene, the title product of melting point 185-186° is obtained (compound no. 1.6).

Workup

  1. washthe organic phase is washed three times
  2. dry with materialdried over sodium sulfate
  3. customthe solvent is removed on a rotary evaporator
  4. customAfter the residue has been recrystallized from toluene

Sources & evidence

ORD record
ord-3f9451a7f5c54cd4bee773f959deb221
Source dataset
uspto-grants-2002_07
Patent number
US06417386B2

Reaction notes

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