Potassium Carbonate → HCID 54364994, compound

HRID 1646465Notes

Reaction equation

HRID 1646465 reaction equation
[CH3:1][O:2][C:3](=[O:18])[CH:4]([S:8][C:9]1[CH:14]=[C:13]([NH2:15])[C:12]([F:16])=[CH:11][C:10]=1[Cl:17])[CH2:5][CH2:6]Br.C(=O)([O-])[O-].[K+].[K+]>S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC.C1(C)C=CC=CC=1>[CH3:1][O:2][C:3]([C:4]1([S:8][C:9]2[CH:14]=[C:13]([NH2:15])[C:12]([F:16])=[CH:11][C:10]=2[Cl:17])[CH2:6][CH2:5]1)=[O:18]

Participants

5

Reactant 2

HCID 11430Potassium CarbonateHCID 539357242-(5-Amino-2-chloro-4-fluorophenylthio)-4-bromobutyric acid methyl ester

Product 1

HCID 54364994HCID 54364994, compoundYield 175.9%

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-bromobutyric acid methyl ester, 30.4 g of potassium carbonate and 1.7 g of tetrabutylammonium hydrogen sulfate in 38 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 yields 17 g of 1-(5-amino-2-chloro-4-fluorophenylthio)-cyclopropanecarboxylic acid methyl ester having a melting point of from +119° to +124° 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

Sources & evidence

ORD record
ord-20af30138ab34984b194433bfee10e31
Source dataset
uspto-grants-1993_01
Patent number
US05180418

Reaction notes

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