1,2-Dimethylhydrazine dihydrochloride → N-(4-Chlorophenyl)-1,2-dimethylhydrazine-1-carbothioamide

HRID 1981336Notes

Reaction equation

HRID 1981336 reaction equation
[OH-].[Na+].Cl.Cl.[CH3:5][NH:6][NH:7][CH3:8].[Cl:9][C:10]1[CH:15]=[CH:14][C:13]([N:16]=[C:17]=[S:18])=[CH:12][CH:11]=1>O.C(O)C>[Cl:9][C:10]1[CH:15]=[CH:14][C:13]([NH:16][C:17]([N:6]([CH3:5])[NH:7][CH3:8])=[S:18])=[CH:12][CH:11]=1

Participants

6

Reactant 3

HCID 93801,2-Dimethylhydrazine dihydrochlorideHCID 14798Sodium HydroxideHCID 164804-Chlorophenyl isothiocyanate

Product 1

HCID 13456645N-(4-Chlorophenyl)-1,2-dimethylhydrazine-1-carbothioamideYield 38.9%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

To a stirred solution of sodium hydroxide (6.1 g, 0.15 mole) in 40 ml of water and 250 ml of ethanol was added N,N'-dimethylhydrazine dihydrochloride (10 g, 0.076 mole). The reaction mixture was warmed to 50° C., and 4-chlorophenylisothiocyanate (12.8 g, 0.076 mole) was added in small portions. Upon complete addition, the reaction mixture was heated under reflux for two hours and then allowed to cool. The cooled reaction mixture was filtered and the filtrate concentrated under reduced pressure to remove most of the solvent. The concentrate was taken up in 200 ml of toluene. The toluene was removed under reduced pressure. This procedure was repeated with two additional 200 ml portions of toluene to remove the remaining ethanol and water traces by azeotropic distillation. The brown residual oil was recrystallized twice from ethanol to give N-(4-chlorophenyl)-1,2-dimethylhydrazinecarbothioamide (6.8 g, mp 103°-104° C.). The nmr spectrum of the product was consistent with the assigned structure.

Workup

  1. additionUpon complete addition
  2. temperaturethe reaction mixture was heated
  3. temperatureunder reflux for two hours
  4. temperatureto cool
  5. customThe cooled reaction mixture
  6. filtrationwas filtered
  7. concentrationthe filtrate concentrated under reduced pressure
  8. customto remove most of the solvent
  9. customThe toluene was removed under reduced pressure
  10. customto remove the remaining ethanol and water traces
  11. distillationby azeotropic distillation
  12. customThe brown residual oil was recrystallized twice from ethanol

Sources & evidence

ORD record
ord-d41151b6c6e2460c90c5397f9f232bac
Source dataset
uspto-grants-1985_04
Patent number
US04514419

Reaction notes

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