Potassium Carbonate → 1-(5-Amino-2-chloro-4-fluorophenylthio)-cyclopropanecarboxylic acid ethyl ester

HRID 1646463Notes

Reaction equation

HRID 1646463 reaction equation
[CH2:1]([O:3][C:4](=[O:19])[CH:5]([S:9][C:10]1[CH:15]=[C:14]([NH2:16])[C:13]([F:17])=[CH:12][C:11]=1[Cl:18])[CH2:6][CH2:7]Cl)[CH3:2].C(=O)([O-])[O-].[K+].[K+]>S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC.C1(C)C=CC=CC=1>[CH2:1]([O:3][C:4]([C:5]1([S:9][C:10]2[CH:15]=[C:14]([NH2:16])[C:13]([F:17])=[CH:12][C:11]=2[Cl:18])[CH2:7][CH2:6]1)=[O:19])[CH3:2]

Participants

5

Reactant 2

HCID 11430Potassium CarbonateHCID 542168052-(5-Amino-2-chloro-4-fluorophenylthio)-4-chlorobutyric acid ethyl ester

Product 1

HCID 537632591-(5-Amino-2-chloro-4-fluorophenylthio)-cyclopropanecarboxylic acid ethyl ester

Reagents, catalysts & solvents 2

HCID 94433Tetrabutylammonium hydrogen sulfateCatalystHCID 1140TolueneSolvent

Procedure

A mixture of 12.5 g of 2-(5-amino-2-chloro-4-fluorophenylthio)-4-chlorobutyric acid ethyl ester, 10.6 g of potassium carbonate and 0.7 g of tetrabutylammonium hydrogen sulfate in 14 ml of toluene is maintained at +80° C. for 40 hours. The solid portions of the reaction mixture are then filtered off and washed with acetone. Evaporation of the solvent and recrystallisation from n-hexane and a small amount of ethyl acetate yield 7.9 g of 1-(5-amino-2-chloro-4-fluoro-phenylthio)-cyclopropanecarboxylic acid ethyl ester having a melting point of from +96° to +97° C.

Workup

  1. temperatureis maintained at +80° C. for 40 hours
  2. filtrationThe solid portions of the reaction mixture are then filtered off
  3. washwashed with acetone
  4. customEvaporation of the solvent and recrystallisation from n-hexane
  5. customof from +96° to +97° C.

Sources & evidence

ORD record
ord-daf7950f171b47bfb3325269a4601b78
Source dataset
uspto-grants-1993_01
Patent number
US05180418

Reaction notes

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