Thionyl Chloride → 3-(4'-Fluoro-4-biphenylyl)-3-methyl-pyrazolidin-5-one

HRID 1576421Notes

Reaction equation

HRID 1576421 reaction equation
C([O:3][C:4](=O)[CH2:5][C:6](Cl)([C:8]1[CH:13]=[CH:12][C:11]([C:14]2[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=2)=[CH:10][CH:9]=1)[CH3:7])C.O=S(Cl)Cl.S(O)(O)(=O)=O.[NH2:32][NH2:33].CC[O-].[Na+]>C(O)C>[F:20][C:17]1[CH:18]=[CH:19][C:14]([C:11]2[CH:12]=[CH:13][C:8]([C:6]3([CH3:7])[CH2:5][C:4](=[O:3])[NH:33][NH:32]3)=[CH:9][CH:10]=2)=[CH:15][CH:16]=1

Participants

6

Reactant 4

HCID 24386Thionyl ChlorideHCID 24842Hydrazine SulfateHCID 2723922Sodium ethoxideHCID 540625593-Chloro-3-(4'-fluoro-4-biphenylyl)-butyric acid ethyl ester

Product 1

HCID 215126753-(4'-Fluoro-4-biphenylyl)-3-methyl-pyrazolidin-5-one

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 32.1 g of 3-chloro-3-(4'-fluoro-4-biphenylyl)-butyric acid ethyl ester (obtainable from the hydroxy ester and SOCl2), 15 g of hydrazine sulfate and 20.5 g of sodium ethylate in 500 ml of absolute ethanol is boiled for 2 hours and the solvent is evaporated. Working up gives 3-(4'-fluoro-4-biphenylyl)-3-methyl-pyrazolidin-5-one, m.p. 194°-196°.

Workup

  1. customthe solvent is evaporated

Sources & evidence

ORD record
ord-e3dca0e911084cf5913ae87adfc6c05c
Source dataset
uspto-grants-1976_09
Patent number
US03980795

Reaction notes

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