Hydrazine → 3-(Methylsulfonyl)benzohydrazide

HRID 877625Notes

Reaction equation

HRID 877625 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].[NH2:15][NH2:16]>CO>[CH3:1][S:2]([C:5]1[CH:6]=[C:7]([CH:12]=[CH:13][CH:14]=1)[C:8]([NH:15][NH2:16])=[O:9])(=[O:4])=[O:3]

Participants

4

Reactant 2

HCID 9321HydrazineHCID 6432252Methyl 3-(methylsulfonyl)benzoate

Product 1

HCID 167825273-(Methylsulfonyl)benzohydrazideYield 80%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
70 °C

Procedure

Methyl 3-(methylsulfonyl)benzoate (100 mg, 0.467 mmol) was added to hydrazine (22.44 mg, 0.700 mmol)) in methanol (10 mL) and refluxed for 12 h at 70° C. The reaction was monitored by TLC. Upon completion of the reaction and following cooling, the solvent was removed by vacuum, and the compound was purified by flash column chromatography (3% CH3OH/CH2Cl2) affording the title compound (80 mg, 80% yield) as a solid. 1H NMR (400 MHz, CDCl3): δ 8.28 (s, 1H), 8.07 (d, 1H, J=7.6 Hz), 8.01 (d, 1H, J=7.6 Hz), 7.62 (t, 1H, J=7.6 Hz), 3.04 (s, 3H). ESI-MS: 215.1 [M+H]+.

Workup

  1. customUpon completion of the reaction
  2. temperaturefollowing cooling
  3. customthe solvent was removed by vacuum
  4. customthe compound was purified by flash column chromatography (3% CH3OH/CH2Cl2)

Sources & evidence

ORD record
ord-870a927dbefa4f9fb53e03292fb3b701
Source dataset
uspto-grants-2015_03
Patent number
US08987335B2

Reaction notes

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