Hydrazine hydrate (1:1) → 3-(Methylsulfonyl)benzohydrazide

HRID 877435Notes

Reaction equation

HRID 877435 reaction equation
[CH3:1][S:2]([C:5]1[CH:6]=[C:7]([CH:12]=[CH:13][CH:14]=1)[C:8](OC)=[O:9])(=[O:4])=[O:3].O.[NH2:16][NH2:17]>C(O)C>[CH3:1][S:2]([C:5]1[CH:6]=[C:7]([CH:12]=[CH:13][CH:14]=1)[C:8]([NH:16][NH2:17])=[O:9])(=[O:4])=[O:3]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 6432252Methyl 3-(methylsulfonyl)benzoate

Product 1

HCID 167825273-(Methylsulfonyl)benzohydrazideYield 95.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A stirred solution of compound 2 (2.1 g, 9.8 mmol) and hydrazine hydrate (2.4 mL, 49.0 mmol) in ethanol (70 mL) was heated to reflux for 8 h. On completion, solvent was removed, diluted with water (30 mL) and extracted with 10% methanol in dichloromethane (60 mL×4). The combined organic layer was washed with brine, dried over sodium sulphate and concentrated to afford the title compound 3 (2.0 g, 91%) which was used for further reaction.

Workup

  1. temperatureto reflux for 8 h
  2. customOn completion, solvent was removed
  3. additiondiluted with water (30 mL)
  4. extractionextracted with 10% methanol in dichloromethane (60 mL×4)
  5. washThe combined organic layer was washed with brine
  6. dry with materialdried over sodium sulphate
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-6f957611072249b1af557b541b46ba37
Source dataset
uspto-grants-2015_03
Patent number
US08987318B2

Reaction notes

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