Acetic Anhydride → acetic acid N'-(2-benzenesulfonyl-acetyl)-hydrazide

HRID 602768Notes

Reaction equation

HRID 602768 reaction equation
[C:1]1([S:7]([CH2:10][C:11]([NH:13][NH2:14])=[O:12])(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:15](OC(=O)C)(=[O:17])[CH3:16]>C(O)(=O)C.O>[C:1]1([S:7]([CH2:10][C:11]([NH:13][NH:14][C:15](=[O:17])[CH3:16])=[O:12])(=[O:8])=[O:9])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 2

HCID 7918Acetic AnhydrideHCID 11378890Benzenesulfonyl-acetic acid hydrazide

Product 1

HCID 11402609acetic acid N'-(2-benzenesulfonyl-acetyl)-hydrazideYield 78%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

To a stirred solution of 1.50 g (7.0 mmol) of benzenesulfonyl-acetic acid hydrazide in 5 mL of acetic acid, 1.44 g (14.0 mmol, 2 eq) of acetic anhydride were added, and the solution was heated at reflux for 1 hour. The reaction mixture was diluted with water, extracted with EtOAc, the organic phase dried over Na2SO4, filtered and evaporated, to afford 1.40 g (78%) of acetic acid N′-(2-benzenesulfonyl-acetyl)-hydrazide as a white solid, MS: 274 (MNH4+).

Workup

  1. temperaturethe solution was heated
  2. temperatureat reflux for 1 hour
  3. extractionextracted with EtOAc
  4. dry with materialthe organic phase dried over Na2SO4
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-ed18b2beae7b42f2abbbcc769bad7030
Source dataset
uspto-grants-2011_03
Patent number
US07906546B2

Reaction notes

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