Hydrazine → HCID 71258151, compound

HRID 877646Notes

Reaction equation

HRID 877646 reaction equation
[S:1]([C:5]1[CH:6]=[C:7]([CH:12]=[CH:13][CH:14]=1)[C:8](OC)=[O:9])(=[O:4])(=[O:3])[NH2:2].[NH2:15][NH2:16]>CO>[NH:15]([C:8]([C:7]1[CH:6]=[C:5]([S:1]([NH2:2])(=[O:4])=[O:3])[CH:14]=[CH:13][CH:12]=1)=[O:9])[NH2:16]

Participants

4

Reactant 2

HCID 9321HydrazineHCID 108836Benzoic acid, 3-(aminosulfonyl)-, methyl ester

Product 1

HCID 71258151HCID 71258151, compoundYield 50.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
65 °C

Procedure

Methyl 3-sulfamoylbenzoate (110 mg, 0.511 mmol) was added to the hydrazine (32.8 mg, 1.022 mmol) in methanol and refluxed for 8 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 flash chromatography (5% methanol/DCM) to yield the 3-(hydrazinecarbonyl)benzenesulfonamide (57 mg, 0.260 mmol, 50.8% yield) as a white solid. 1H NMR (CD3OD, 400 MHz): δ 8.32 (m, 1H), 8.04 (d, 1H, J=7.6 Hz), 7.97 (d, 1H, J=7.6 Hz), 7.63 (t, 1H, J=8.0 Hz). Mass [M+H]+:216.0

Workup

  1. temperatureFollowing cooling
  2. customreaction
  3. customAfter completion of the reaction
  4. customthe solvent was removed by vacuum
  5. customcompound was purified by flash chromatography (5% methanol/DCM)

Sources & evidence

ORD record
ord-1284525798bd4ea7aea67168f1706239
Source dataset
uspto-grants-2015_03
Patent number
US08987335B2

Reaction notes

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