Benzenesulfonyl chloride → Hydrazinecarboxylic acid, 2-(phenylsulfonyl)-, methyl ester

HRID 596926Notes

Reaction equation

HRID 596926 reaction equation
[C:1]([O:5][CH3:6])(=[O:4])[NH:2][NH2:3].C(=O)(O)[O-].[Na+].[C:12]1([S:18](Cl)(=[O:20])=[O:19])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>O>[C:12]1([S:18]([NH:3][NH:2][C:1]([O:5][CH3:6])=[O:4])(=[O:20])=[O:19])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

5

Reactant 3

HCID 7369Benzenesulfonyl chlorideHCID 80519Methyl carbazateHCID 516892Sodium Bicarbonate

Product 1

HCID 8501001Hydrazinecarboxylic acid, 2-(phenylsulfonyl)-, methyl ester

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

180 g. (0.2 mole) of methyl carbazate (from hydrazine and dimethyl carbonate) is placed in a liter flask. 20.0 g. (0.24 mole) of sodium bicarbonate and 100 ml. water are added. The mixture is stirred and dropped in 35.2 g. (0.2 mole) of benzene sulfonyl chloride. Then the mixture is stirred for 16 hours. The crystals that have formed are filtered off, washed with water, and dried in air. Yield = 34.5 g.; m.p. 149°-154° C. Upon recrystallization from ethanol 26 g. of material is recovered which melts sharply at 155° C.

Workup

  1. additiondropped in 35.2 g
  2. stirringThen the mixture is stirred for 16 hours
  3. customThe crystals that have formed
  4. filtrationare filtered off
  5. washwashed with water
  6. customdried in air
  7. customUpon recrystallization from ethanol 26 g
  8. customof material is recovered which melts sharply at 155° C.

Sources & evidence

ORD record
ord-1858ef5995844c61bd709e1ae8ad3f5f
Source dataset
uspto-grants-1977_03
Patent number
US04012432

Reaction notes

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