Methylhydrazine → N-(2-benzoyl-4-chlorophenyl)-methyl-hydrazinecarbothioamide

HRID 1732201Notes

Reaction equation

HRID 1732201 reaction equation
[C:1]([C:9]1[CH:14]=[C:13]([Cl:15])[CH:12]=[CH:11][C:10]=1[N:16]=[C:17]=[S:18])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:19][NH:20][NH2:21].[N-]=C=S>C(OCC)C>[C:1]([C:9]1[CH:14]=[C:13]([Cl:15])[CH:12]=[CH:11][C:10]=1[NH:16][C:17]([N:20]([CH3:19])[NH2:21])=[S:18])(=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 6061MethylhydrazineHCID 5200219Sbb012730HCID 178418790HCID 178418790, compound

Product 1

HCID 13972523N-(2-benzoyl-4-chlorophenyl)-methyl-hydrazinecarbothioamideYield 91%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent3×

Procedure

A solution of 5.48 grams (0.02 mole) of 2-benzoyl-4-chlorophenylisothiocyanate in about 50 ml of ethyl ether was added dropwise to a solution containing 1.5 ml (0.028 mole) of methyl hydrazine (98%) in about 50 ml of ethyl ether cooled in an ice bath. Additional ethyl ether was added to facilitate stirring. Following addition of the isothiocyanate, the reaction mixture was stirred at room temperature for about 30 minutes. The solid was collected and washed with additional ethyl ether to yield 5.82 grams (91% yield) of N-(2-benzoyl-4-chlorophenyl)-methyl-hydrazinecarbothioamide as a white solid. The melting point was found to be 168.5°-170° C.

Workup

  1. temperaturecooled in an ice bath
  2. stirringthe reaction mixture was stirred at room temperature for about 30 minutes
  3. customThe solid was collected
  4. washwashed with additional ethyl ether

Sources & evidence

ORD record
ord-69fa5faf7eff45adae4cccccb2a208c6
Source dataset
uspto-grants-1980_12
Patent number
US04237049

Reaction notes

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