Methyl iodide → 2-(4-Chloro-2-fluorophenyl)-2,3,4,5,6,7-hexahydro-3-methylthio-1H-isoindol-1-one

HRID 647406Notes

Reaction equation

HRID 647406 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH:16]([SH:17])[C:15]3[CH2:14][CH2:13][CH2:12][CH2:11][C:10]=3[C:9]2=[O:18])=[C:4]([F:19])[CH:3]=1.CI.[C:22](=O)([O-])[O-].[K+].[K+]>CC(C)=O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH:16]([S:17][CH3:22])[C:15]3[CH2:14][CH2:13][CH2:12][CH2:11][C:10]=3[C:9]2=[O:18])=[C:4]([F:19])[CH:3]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 132575922-(4-chloro-2-fluorophenyl)-2,3,4,5,6,7-hexahydro-3-mercapto-1H-isoindol-1-one

Product 1

HCID 132575932-(4-Chloro-2-fluorophenyl)-2,3,4,5,6,7-hexahydro-3-methylthio-1H-isoindol-1-oneYield 90%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

In 10 ml of acetone was dissolved 1.5 g of 2-(4-chloro-2-fluorophenyl)-2,3,4,5,6,7-hexahydro-3-mercapto-1H-isoindol-1-one, and 1.5 g of methyl iodide and 1.3 g of potassium carbonate were added to the solution, followed by stirring at 40° to 50° C. for 5 hours. After cooling, the insoluble matter was filtered out, and the filtrate was concentrated under reduced pressure. The residual, oily substance was purified by means of column chromatography with the use of silica gel (developing solvent of acetone-hexane), thereby producing 1.4 g (yield of 90%) of the subject compound in white crystals, m.p. 97°-98° C.

Workup

  1. additionwere added to the solution
  2. temperatureAfter cooling
  3. filtrationthe insoluble matter was filtered out
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. customThe residual, oily substance was purified by means of column chromatography with the use of silica gel (developing solvent of acetone-hexane)

Sources & evidence

ORD record
ord-2ff3a6e31fa4443d9f038cfd82ecab4f
Source dataset
uspto-grants-1983_10
Patent number
US04409018

Reaction notes

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