Water → 4,5-Dichloro-N'-phenyl-1H-imidazole-2-carbohydrazide

HRID 1447966Notes

Reaction equation

HRID 1447966 reaction equation
CS[C:3]([C:5]1[NH:6][C:7]([Cl:11])=[C:8]([Cl:10])[N:9]=1)=[O:4].[C:12]1([NH:18][NH2:19])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.O>C(O)C>[C:12]1([NH:18][NH:19][C:3]([C:5]2[NH:6][C:7]([Cl:11])=[C:8]([Cl:10])[N:9]=2)=[O:4])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

5

Reactant 3

HCID 962WaterHCID 7516PhenylhydrazineHCID 536468924,5-dichloro-imidazole-2-thiocarboxylic acid S-methyl ester

Product 1

HCID 540087254,5-Dichloro-N'-phenyl-1H-imidazole-2-carbohydrazideYield 50%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

21.1 g (0.1 mol) of 4,5-dichloro-imidazole-2-thiocarboxylic acid S-methyl ester were boiled with 10.8 g (0.1 mol) of phenylhydrazine in 150 ml of ethanol for 4 hours under reflux. The cooled reaction mixture was mixed with 500 ml of water and the crystals which had separated out were filtered off and dried. 13.5 g (50% of theory) of 4,5-dichloro-imidazole-2-carboxylic acid N'-phenyl-hydrazide with a melting point of 229°-230° C. (from ethyl acetate) were obtained.

Workup

  1. temperatureunder reflux
  2. customThe cooled reaction mixture
  3. customthe crystals which had separated out
  4. filtrationwere filtered off
  5. customdried

Sources & evidence

ORD record
ord-292accddab874fae84801bd250e8ae1c
Source dataset
uspto-grants-1979_12
Patent number
US04179277

Reaction notes

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