Water → 2-(4-Chloro-2-fluorophenyl)-2,3,4,5,6,7-hexahydro-3-methoxycarbonylthio-1H-isoindol-1-one

HRID 647412Notes

Reaction equation

HRID 647412 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.Cl[C:21]([O:23][CH3:24])=[O:22].O>N1C=CC=CC=1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH:16]([S:17][C:21]([O:23][CH3:24])=[O: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 962WaterHCID 6586Methyl chloroformateHCID 132575922-(4-chloro-2-fluorophenyl)-2,3,4,5,6,7-hexahydro-3-mercapto-1H-isoindol-1-one

Product 1

HCID 132575962-(4-Chloro-2-fluorophenyl)-2,3,4,5,6,7-hexahydro-3-methoxycarbonylthio-1H-isoindol-1-oneYield 84%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

In 20 ml of pyridine was dissolved 3.0 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 chloroformate was added to the solution with stirring with cooling at 5° to 10° C. over a period of 20 minutes. After stirring was effected at the same temperature for 2 hours and then at room temperature for 1 hour, the reaction solution was treated with water, and extracted with dichloromethane, followed by washing with dilute hydrochloric acid and water, successively, and drying over anhydrous sodium sulfate. The dichloromethane was distilled off under reduced pressure, and the residual, oily substance was purified by means of column chromatography with the use of silica gel (developing solvent of acetone-hexane), thereby producing 3.0 g (yield of 84%) of the subject compound in white crystals, m.p. 80°-81° C.

Workup

  1. additionwas added to the solution
  2. temperaturewith cooling at 5° to 10° C. over a period of 20 minutes
  3. stirringAfter stirring
  4. waitat room temperature for 1 hour
  5. extractionextracted with dichloromethane
  6. washby washing with dilute hydrochloric acid and water
  7. dry with materialsuccessively, and drying over anhydrous sodium sulfate
  8. distillationThe dichloromethane was distilled off under reduced pressure
  9. 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-607b48f8b9a64c57a7d07f6fa99c02b9
Source dataset
uspto-grants-1983_10
Patent number
US04409018

Reaction notes

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