Potassium Hydroxide → HCID 19800626, compound

HRID 1646458Notes

Reaction equation

HRID 1646458 reaction equation
[OH-].[K+].C([O:5][C:6](=[O:21])[CH:7]([S:11][C:12]1[CH:17]=[C:16]([NH2:18])[C:15]([F:19])=[CH:14][C:13]=1[Cl:20])[CH2:8][CH2:9]Cl)C>C(O)C>[NH2:18][C:16]1[C:15]([F:19])=[CH:14][C:13]([Cl:20])=[C:12]([S:11][C:7]2([C:6]([OH:5])=[O:21])[CH2:8][CH2:9]2)[CH:17]=1

Participants

4

Reactant 2

HCID 14797Potassium Hydroxide2×HCID 542168052-(5-Amino-2-chloro-4-fluorophenylthio)-4-chlorobutyric acid ethyl ester

Product 1

HCID 19800626HCID 19800626, compoundYield 73.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

A solution of 2.4 g of potassium hydroxide in 50 ml of ethanol is added dropwise while stirring at a temperature of +5° C. to a solution of 14.2 g of 2-(5-amino-2-chloro-4-fluorophenylthio)-4-chlorobutyric acid ethyl ester in 25 ml of ethanol. After stirring for 18 hours, 0.9 g of potassium hydroxide is added a further 3 times, and the reaction mixture is stirred for 6 hours each time until the reaction is complete. The reaction mixture is then concentrated, water is added and extraction is carried out 3 times with ethyl acetate. The combined organic phases are dried over sodium sulfate and then concentrated by evaporation. Recrystallisation of the residue from ethyl acetate/n-hexane yields 8.4 g of 1-(5-amino-2-chloro-4-fluoro-phenylthio)-cyclopropanecarboxylic acid having a melting point of from +266° to +267° C.

Workup

  1. stirringthe reaction mixture is stirred for 6 hours each time until the reaction
  2. concentrationThe reaction mixture is then concentrated
  3. additionwater is added
  4. extractionextraction
  5. dry with materialThe combined organic phases are dried over sodium sulfate
  6. concentrationconcentrated by evaporation
  7. customRecrystallisation of the residue from ethyl acetate/n-hexane

Sources & evidence

ORD record
ord-980051065d1045af88b6b9bee73af63e
Source dataset
uspto-grants-1993_01
Patent number
US05180418

Reaction notes

Loading…