Hydrazine → 3-(Hydrazinecarbonyl)-N,N-dimethylbenzene-1-sulfonamide

HRID 1777025Notes

Reaction equation

HRID 1777025 reaction equation
[CH3:1][N:2]([CH3:16])[S:3]([C:6]1[CH:7]=[C:8]([CH:13]=[CH:14][CH:15]=1)[C:9](OC)=[O:10])(=[O:5])=[O:4].[NH2:17][NH2:18]>CO>[NH:17]([C:9]([C:8]1[CH:7]=[C:6]([S:3]([N:2]([CH3:16])[CH3:1])(=[O:5])=[O:4])[CH:15]=[CH:14][CH:13]=1)=[O:10])[NH2:18]

Participants

4

Reactant 2

HCID 9321HydrazineHCID 1262217Methyl 3-(dimethylsulfamoyl)benzoate

Product 1

HCID 38489513-(Hydrazinecarbonyl)-N,N-dimethylbenzene-1-sulfonamideYield 40%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
65 °C

Procedure

Methyl 3-(N,N-dimethylsulfamoyl)benzoate (150 mg, 0.617 mmol) was added to hydrazine (29.6 mg, 0.925 mmol) in methanol (10 mL) and refluxed for 8 h at 65° C. Following cooling, the reaction was monitored by TLC. After completion of the reaction, the solvent was removed by vacuum and the compound was purified by column chromatography affording the title compound (60 mg). 1H NMR (400 MHz, CDCl3): δ 8.11 (s, 1H), 8.01 (d, 1H, J=8.4 Hz), 7.92 (d, 1H, J=8.0 Hz), 7.65 (t, 1H, J=8.0 Hz), 2.73 (5, 6H). ESI-MS: 244.0 [M+H]+.

Workup

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

Sources & evidence

ORD record
ord-18ce74612b254928b6340d4c70e685ea
Source dataset
uspto-grants-2016_02
Patent number
US09266838B2

Reaction notes

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