Hydrazine → N-aminobenzenecarbothioamide

HRID 1039166

Reaction equation

HRID 1039166 reaction equation
COC(=O)C[S:5][C:6](=S)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[NH2:15][NH2:16]>C(O)C>[C:6]([NH:15][NH2:16])(=[S:5])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

4

Reactant 2

HCID 9321HydrazineHCID 71356278Methyl 2-((phenylcarbonothioyl)thio)acetate

Product 1

HCID 3361911N-aminobenzenecarbothioamideYield 94%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Add a solution of thiobenzoylsulfanylacetic acid methyl ester (1.9 g, 8.4 mmol) in ethanol (30 mL) to a solution of anhydrous hydrazine (1 mL) at room temperature under nitrogen and stir for 2 hours. Then add water (20 mL) and remove the solvent under reduced pressure. Dissolve the residue in ethyl acetate (300 mL), wash with water (200 mL) and brine (200 mL), and dry over magnesium sulfate. Remove the solvent under reduced pressure to provide thiobenzoic acid hydrazide (1.2 g, 94%).

Workup

  1. customThen add water (20 mL) and remove the solvent under reduced pressure
  2. dissolutionDissolve the residue in ethyl acetate (300 mL)
  3. washwash with water (200 mL) and brine (200 mL)
  4. dry with materialdry over magnesium sulfate
  5. customRemove the solvent under reduced pressure

Sources & evidence

ORD record
ord-e4fcfebd8f5843d19cbaa5f7df69b2d0
Source dataset
uspto-grants-2013_10
Patent number
US08552039B2

Linked notes

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