Hydrazine hydrate (1:1) → 4-Methoxythiophene-3-carbohydrazide

HRID 2107619Notes

Reaction equation

HRID 2107619 reaction equation
[CH3:1][O:2][C:3]1[C:4]([C:8]([O:10]C)=O)=[CH:5][S:6][CH:7]=1.O.[NH2:13][NH2:14]>CO>[CH3:1][O:2][C:3]1[C:4]([C:8]([NH:13][NH2:14])=[O:10])=[CH:5][S:6][CH:7]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 2778377Methyl 4-methoxythiophene-3-carboxylate

Product 1

HCID 27367824-Methoxythiophene-3-carbohydrazide

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Methyl 4-methoxy-3-thiophenecarboxylate (50.8 g, 0.295 mol) was refluxed with hydrazine hydrate (30 ml) in methanol (250 ml) overnight. The solvent was evaporated and the residue was diluted with water (300 ml) and extracted with dichloromethane (5×100 ml). The dichloromethane extracts were dried over sodium sulfate, filtered and evaporated under reduced pressure to give the title compound as an off white solid, 49.5 g, m.p. 91°-92°.

Workup

  1. customThe solvent was evaporated
  2. additionthe residue was diluted with water (300 ml)
  3. extractionextracted with dichloromethane (5×100 ml)
  4. dry with materialThe dichloromethane extracts were dried over sodium sulfate
  5. filtrationfiltered
  6. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-4e587da415784b03abc3e73dd4a2c545
Source dataset
uspto-grants-1990_06
Patent number
US04935431

Reaction notes

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