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

HRID 877610Notes

Reaction equation

HRID 877610 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 (s, 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-801770c7005246b4ac17748c4cdd1d00
Source dataset
uspto-grants-2015_03
Patent number
US08987335B2

Reaction notes

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