Ethyl Acetate → N-[3-(Trifluoromethyl)phenyl]hydrazinecarbothioamide

HRID 1851677Notes

Reaction equation

HRID 1851677 reaction equation
[N:1]([C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([C:10]([F:13])([F:12])[F:11])[CH:5]=1)=[C:2]=[S:3].O.[NH2:15][NH2:16].C(OCC)(=O)C>CO.CCCCCC>[F:12][C:10]([F:11])([F:13])[C:6]1[CH:5]=[C:4]([NH:1][C:2]([NH:15][NH2:16])=[S:3])[CH:9]=[CH:8][CH:7]=1

Participants

6

Reactant 3

HCID 8857Ethyl AcetateHCID 24654Hydrazine hydrate (1:1)2×HCID 1372321-Isothiocyanato-3-(trifluoromethyl)benzene

Product 1

HCID 737504N-[3-(Trifluoromethyl)phenyl]hydrazinecarbothioamide

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8058HexaneSolvent

Procedure

To a stirred solution of 1-isothiocyanato-3-(trifluoromethyl)benzene (250 mg, 1.23 mmol) in methanol (5 mL) was added hydrazine hydrate (307 mg, 6.16 mmol) dropwise at 5° C.-10° C. After complete addition of hydrazine hydrate, the reaction mixture was stirred at room temperature for 2-3 h. When TLC (mobile phase-30% ethyl acetate in n-Hexane, Rf. S.M.—0.80, product—0.2) showed absence of starting material, the methanol was concentrated, water was added and extracted with ethyl acetate. The combined organic layer was washed with brine, dried over Na2SO4 and concentrated to give the pure product as an off white solid (Yield: 200 mg, 69.4% of theoretical).

Workup

  1. concentrationthe methanol was concentrated
  2. additionwater was added
  3. extractionextracted with ethyl acetate
  4. washThe combined organic layer was washed with brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated
  7. customto give the pure product as an off white solid (Yield: 200 mg, 69.4% of theoretical)

Sources & evidence

ORD record
ord-1e541ac1819341a88cc259cab845d5a5
Source dataset
uspto-grants-2015_02
Patent number
US08957216B2

Reaction notes

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