Hydrazine → p-Hydrazinobenzenesulphonamide

HRID 2117970Notes

Reaction equation

HRID 2117970 reaction equation
Cl[C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH2:11])(=[O:10])=[O:9])=[CH:4][CH:3]=1.[NH2:12][NH2:13]>O>[NH:12]([C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH2:11])(=[O:10])=[O:9])=[CH:4][CH:3]=1)[NH2:13]

Participants

4

Reactant 2

HCID 9321HydrazineHCID 668244-Chlorobenzenesulfonamide

Product 1

HCID 78105p-HydrazinobenzenesulphonamideYield 95%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A stirred solution of 4-chlorobenzenesulfonamide (38.33 g, 200 mmol) and anhydrous hydrazine (31.4 mL, 1.0 mol) was heated at reflux for 30 hours. After cooling to room temperature, the mixture was poured into water (500 mL) with swirling. The resulting precipitate was collected by filtration, washed thoroughly with water several times, air-dried, and dried under vacuum to give the title compound (35.5 g, 95% yield) as a white solid. Mp 169-171° C. 1H NMR (300 MHz, THF-d8) δ 7.59 (d, J=8.8 Hz, 2H), 6.77 (d, J=8.8 Hz, 2H), 6.62 (br, 1H), 5.99 (br, 2H), 3.87 (br, 2H). Mass spectrum (API-TIS) m/z 188 (MH+).

Workup

  1. temperatureat reflux for 30 hours
  2. filtrationThe resulting precipitate was collected by filtration
  3. washwashed thoroughly with water several times
  4. customair-dried
  5. customdried under vacuum

Sources & evidence

ORD record
ord-cf1b901298f24607830725ac53c173ab
Source dataset
uspto-grants-2008_10
Patent number
US07442802B2

Reaction notes

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