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

HRID 2163570Notes

Reaction equation

HRID 2163570 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 = 34.5g.; 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-520e5d24e6cc4d75b804128ce1bf96f8
Source dataset
uspto-grants-1979_01
Patent number
US04135049

Reaction notes

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