Hydrazine hydrate (1:1) → HCID 13476442, compound

HRID 1981874Notes

Reaction equation

HRID 1981874 reaction equation
C([S:4][CH:5]([CH2:9][C:10](=[O:18])[C:11]1[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][CH:12]=1)[C:6]([OH:8])=[O:7])(=O)C.O.NN>C(OCC)C.C(O)C>[Cl:17][C:14]1[CH:13]=[CH:12][C:11]([C:10]([CH2:9][CH:5]([SH:4])[C:6]([OH:8])=[O:7])=[O:18])=[CH:16][CH:15]=1

Participants

5

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 13476434HCID 13476434, compound

Product 1

HCID 13476442HCID 13476442, compoundYield 41.2%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 3283Diethyl EtherSolvent

Procedure

To a solution of 2.87 g of 2-acetylthio-3-(4-chlorobenzoyl)propionic acid in 50 ml of diethyl ether was added dropwise a solution of 0.95 g of 80% hydrazine hydrate in 5 ml of ethanol under ice-cooling with stirring over a period of 30 minutes. The mixture was stirred for a further 30 minutes. The reaction solution was washed with water and dried over magnesium sulfate. The diethyl ether was removed from the solution by evaporation, and the residue was purified by silica gel column chromatography using a mixture of hexane and diethyl ether as an eluent and recrystallized from the same mixture to give 1.01 g of 3-(4-chlorobenzoyl)-2-mercaptopropionic acid.

Workup

  1. temperaturecooling
  2. stirringThe mixture was stirred for a further 30 minutes
  3. washThe reaction solution was washed with water
  4. dry with materialdried over magnesium sulfate
  5. customThe diethyl ether was removed from the solution by evaporation
  6. customthe residue was purified by silica gel column chromatography
  7. additiona mixture of hexane and diethyl ether as an eluent
  8. customrecrystallized from the same mixture

Sources & evidence

ORD record
ord-ddd44c3340634d50ab2aac6e10695f42
Source dataset
uspto-grants-1986_06
Patent number
US04594197

Reaction notes

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