Ammonium thiocyanate → 2-(4-Chlorophenyl)hydrazine-1-carbothioamide

HRID 2106568Notes

Reaction equation

HRID 2106568 reaction equation
Cl.[Cl:2][C:3]1[CH:8]=[CH:7][C:6]([NH:9][NH2:10])=[CH:5][CH:4]=1.[S-:11][C:12]#[N:13].[NH4+]>C(O)C>[Cl:2][C:3]1[CH:8]=[CH:7][C:6]([NH:9][NH:10][C:12]([NH2:13])=[S:11])=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 15666Ammonium thiocyanateHCID 71600Hydrazine, (4-chlorophenyl)-, hydrochloride (1:1)

Product 1

HCID 27636652-(4-Chlorophenyl)hydrazine-1-carbothioamide

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Fifty g of 4-chlorophenylhydrazine hydrochloride and 40 g of ammonium thiocyanate were added to 250 ml of denatured ethanol and the mixture was stirred under reflux for 16 hours. It was then filtered while still hot and the filter cake was washed with about 100 ml of hot ethanol. As the filtrate cooled, the product began to crystallize, and it was collected and recrystallized from denatured ethanol to obtain 32.7 g of the desired intermediate, m.p. 200°-201°.

Workup

  1. temperatureunder reflux for 16 hours
  2. filtrationIt was then filtered while still hot and the filter cake
  3. washwas washed with about 100 ml of hot ethanol
  4. temperatureAs the filtrate cooled
  5. customto crystallize
  6. customit was collected
  7. customrecrystallized from denatured ethanol

Sources & evidence

ORD record
ord-0f91b2622470487099e99e34da52775f
Source dataset
uspto-grants-1990_06
Patent number
US04931083

Reaction notes

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