Hydrazine hydrate (1:1) → 2-(Aminosulfonyl)benzeneacetic acid, hydrazide

HRID 231973Notes

Reaction equation

HRID 231973 reaction equation
[NH2:1][S:2]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[CH2:11][C:12]([O:14]C)=O)(=[O:4])=[O:3].O.[NH2:17][NH2:18]>C(O)C>[NH2:1][S:2]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[CH2:11][C:12]([NH:17][NH2:18])=[O:14])(=[O:4])=[O:3]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 13064551Methyl 2-(2-sulfamoylphenyl)acetate

Product 1

HCID 159257202-(Aminosulfonyl)benzeneacetic acid, hydrazideYield 76.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a suspension of 30 g of methyl 2-(aminosulfonyl)benzeneacetate in 125 ml of absolute ethanol was added 7.8 g of hydrazine monohydrate. The suspension was heated at reflux for about 16 hours, then cooled in an ice-water bath. A viscous oil formed which solidified on continued stirring and cooling. The suspension was filtered and suction-dried to give 23 g of the subject compound; m.p. 116°-125° C. Anal. Calc. for: C8H11N3O3S; C,41.9; H,4.8; N,18.3. Found: C,41.5; H,4.9; N,18.0.

Workup

  1. temperatureThe suspension was heated
  2. temperatureat reflux for about 16 hours
  3. temperaturecooled in an ice-water bath
  4. customA viscous oil formed which
  5. temperaturecooling
  6. filtrationThe suspension was filtered
  7. customsuction-dried

Sources & evidence

ORD record
ord-72687c20a321481ea6b06225590ca16e
Source dataset
uspto-grants-1989_07
Patent number
US04851030

Reaction notes

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