Methanol → HCID 54364994, compound

HRID 1646466Notes

Reaction equation

HRID 1646466 reaction equation
[NH2:1][C:2]1[C:3]([F:16])=[CH:4][C:5]([Cl:15])=[C:6]([S:8][C:9]2([C:12]([OH:14])=[O:13])[CH2:11][CH2:10]2)[CH:7]=1.[CH3:17]O>S(=O)(=O)(O)O>[CH3:17][O:13][C:12]([C:9]1([S:8][C:6]2[CH:7]=[C:2]([NH2:1])[C:3]([F:16])=[CH:4][C:5]=2[Cl:15])[CH2:11][CH2:10]1)=[O:14]

Participants

4

Reactant 2

HCID 887MethanolHCID 19800626HCID 19800626, compound

Product 1

HCID 54364994HCID 54364994, compound

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidCatalyst

Procedure

A solution of 3.6 g of 1-(5-amino-2-chloro-4-fluorophenylthio)-cyclopropanecarboxylic acid and a few drops of sulfuric acid in 50 ml of methanol is heated under reflux until the starting material can no longer be detected. The methanol is then evaporated off, water and ethyl acetate are added to the residue and the organic phase is washed in succession with sodium hydrogen carbonate solution, water and saturated sodium chloride solution. Concentration and purification of the crude product by means of silica gel chromatography yield 5.7 g of 1-(5-amino-2-chloro-4-fluorophenylthio)-cyclopropanecarboxylic acid methyl ester having a melting point of from +119° to +121° C.

Workup

  1. temperatureunder reflux until the starting material
  2. customThe methanol is then evaporated off
  3. additionwater and ethyl acetate are added to the residue
  4. washthe organic phase is washed in succession with sodium hydrogen carbonate solution, water and saturated sodium chloride solution
  5. concentrationConcentration and purification of the crude product by means of silica gel chromatography yield 5.7 g of 1-(5-amino-2-chloro-4-fluorophenylthio)-cyclopropanecarboxylic acid methyl ester having a melting point of from +119° to +121° C.

Sources & evidence

ORD record
ord-e62f18c31d874f4b8141c63cea525f38
Source dataset
uspto-grants-1993_01
Patent number
US05180418

Reaction notes

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