Hydrazine → 3-(hydrazinecarbonyl)-N-methylbenzenesulfonamide

HRID 1777050Notes

Reaction equation

HRID 1777050 reaction equation
[NH2:1][NH2:2].[CH3:3][NH:4][S:5]([C:8]1[CH:9]=[C:10]([CH:15]=[CH:16][CH:17]=1)[C:11](OC)=[O:12])(=[O:7])=[O:6]>CO>[NH:1]([C:11]([C:10]1[CH:9]=[C:8]([S:5]([NH:4][CH3:3])(=[O:7])=[O:6])[CH:17]=[CH:16][CH:15]=1)=[O:12])[NH2:2]

Participants

4

Reactant 2

HCID 9321HydrazineHCID 9320906Methyl 3-(methylsulfamoyl)benzoate

Product 1

HCID 677513503-(hydrazinecarbonyl)-N-methylbenzenesulfonamideYield 74.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
65 °C

Procedure

Hydrazine (43.3 mg, 1.352 mmol) was added to the methyl 3-(N-methylsulfamoyl)benzoate (155 mg, 0.676 mmol) in methanol and refluxed for 12 h at 65° C. Following cooling, reaction was monitored by TLC. After completion of the reaction, the solvent was removed by vacuum and then compound was purified by column chromatography to yield 3-(hydrazinecarbonyl)-N-methylbenzenesulfonamide (120 mg, 0.502 mmol, 74.3% yield). 1H NMR (CDCl3, 400 MHz): δ 8.25 (m, 1H), 8.01 (m, 2H), 7.64 (m, 2H), 4.63 (m, 1H), 4.17 (m, 2H), 2.69 (d, 3H, J=5.2 Hz). ESI-MS: 230.0 [M+H]+

Workup

  1. temperatureFollowing cooling
  2. customreaction
  3. customAfter completion of the reaction
  4. customthe solvent was removed by vacuum
  5. customcompound was purified by column chromatography

Sources & evidence

ORD record
ord-054bc86bf76c4245b7d8d905f5127334
Source dataset
uspto-grants-2016_02
Patent number
US09266838B2

Reaction notes

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