4-Methylbenzoyl Chloride → Hydrazine, N-(4-methylbenzoyl)-N'-(2-chlorobenzoyl)-

HRID 1732286

Reaction equation

HRID 1732286 reaction equation
[Cl:1][C:2]1[CH:11]=[CH:10][CH:9]=[CH:8][C:3]=1[C:4]([NH:6][NH2:7])=[O:5].[CH3:12][C:13]1[CH:21]=[CH:20][C:16]([C:17](Cl)=[O:18])=[CH:15][CH:14]=1>[OH-].[Na+]>[Cl:1][C:2]1[CH:11]=[CH:10][CH:9]=[CH:8][C:3]=1[C:4]([NH:6][NH:7][C:17](=[O:18])[C:16]1[CH:20]=[CH:21][C:13]([CH3:12])=[CH:14][CH:15]=1)=[O:5]

Participants

4

Reactant 2

HCID 134054-Methylbenzoyl ChlorideHCID 798832-Chlorobenzohydrazide

Product 1

HCID 576801Hydrazine, N-(4-methylbenzoyl)-N'-(2-chlorobenzoyl)-Yield 45.7%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

2-Chlorobenzhydrazide (38.8 g) was dissolved in sodium hydroxide solution (9.18 g in 125 ml water). The solution was stirred and 4-methylbenzoyl chloride (35.2 g) added dropwise. The mixture was then stirred for 2 hours and the solid which precipitated was filtered off, washed with water and recrystallised from ethanol to give 30.0 g of the desired product, mp 204°-206° C.

Workup

  1. stirringThe mixture was then stirred for 2 hours
  2. customthe solid which precipitated
  3. filtrationwas filtered off
  4. washwashed with water
  5. customrecrystallised from ethanol

Sources & evidence

ORD record
ord-d8a71e66e56440d39d5a5d1b640bf930
Source dataset
uspto-grants-1980_12
Patent number
US04237127

Linked notes

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