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

HRID 647408Notes

Reaction equation

HRID 647408 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[CH2:21][C:22](=[O:24])[CH3:23].O.ClCCl>N1C=CC=CC=1>[CH2:21]([S:17][CH:16]1[C:15]2[CH2:14][CH2:13][CH2:12][CH2:11][C:10]=2[C:9](=[O:18])[N:8]1[C:5]1[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][C:4]=1[F:19])[C:22]([CH3:23])=[O:24]

Participants

6

Reactant 4

HCID 962WaterHCID 6344DichloromethaneHCID 6571ChloroacetoneHCID 132575922-(4-chloro-2-fluorophenyl)-2,3,4,5,6,7-hexahydro-3-mercapto-1H-isoindol-1-one

Product 1

HCID 132575943-Acetonylthio-2-(4-chloro-2-fluorophenyl)-2,3,4,5,6,7-hexahydro-1H-isoindol-1-oneYield 73%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

In 10 ml pyridine 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 0.6 g of chloroacetone was added dropwise to the mixture with stirring with cooling at 5° to 10° C. over a period of 10 minutes. After cooling was continued at room temperature for 2 hours, water was added to the mixture for extraction with dichloromethane. The dichloromethane layer was separated out, washed with dilute hydrochloric acid and water, successively, and dried over anhydrous sodium sulfate. The dichloromethane was distilled off under reduced pressure, and the resulting crystals were washed with a mixed solvent of ether and hexane and dried, thereby producing 1.3 g (yield of 73%) of the subject compound. Recrystallization from ethanol yielded white crystals, m.p. 131°-132° C.

Workup

  1. additionwas added dropwise to the mixture
  2. temperaturewith cooling at 5° to 10° C. over a period of 10 minutes
  3. temperatureAfter cooling
  4. customThe dichloromethane layer was separated out
  5. washwashed with dilute hydrochloric acid and water
  6. dry with materialsuccessively, and dried over anhydrous sodium sulfate
  7. distillationThe dichloromethane was distilled off under reduced pressure
  8. washthe resulting crystals were washed with a mixed solvent of ether and hexane
  9. customdried

Sources & evidence

ORD record
ord-57e264504aa84c9680ad41f0026ef81d
Source dataset
uspto-grants-1983_10
Patent number
US04409018

Reaction notes

Loading…