Thionyl Chloride → 3-Chloro-2-(4-chloro-2-fluorophenyl)-2,3,4,5,6,7-hexahydro-1H-isoindol-1-one

HRID 647404Notes

Reaction equation

HRID 647404 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH:16]([OH:17])[C:15]3[CH2:14][CH2:13][CH2:12][CH2:11][C:10]=3[C:9]2=O)=[C:4]([F:19])[CH:3]=1.S(Cl)([Cl:22])=O>ClCCl>[Cl:22][CH:9]1[C:10]2[CH2:11][CH2:12][CH2:13][CH2:14][C:15]=2[C:16](=[O:17])[N:8]1[C:5]1[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][C:4]=1[F:19]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 13257633HCID 13257633, compound

Product 1

HCID 132576323-Chloro-2-(4-chloro-2-fluorophenyl)-2,3,4,5,6,7-hexahydro-1H-isoindol-1-oneYield 87%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In 30 ml of dichloromethane was suspended 21.0 g of 2-(4-chloro-2-fluorophenyl)-3-hydroxy-2,3,4,5,6,7-hexahydro-1H-isoindol-1-one, and 7.5 ml of thionyl chloride was added to the suspension under stirring over a 20-minute period. The reaction mixture was warmed, stirred at 40° to 45° C. for 1 hour and concentrated to dryness under reduced pressure. The residue was dissolved in methylene chloride and, upon addition of hexane, there was produced insoluble matter, which was filtered out. The filtrate was concentrated to dryness under reduced pressure, thereby affording 19.5 g (yield of 87%) of crystals of the subject compound. Recrystallization from cyclohexane yielded white crystals, m.p. 89°-90° C.

Workup

  1. additionwas added to the suspension
  2. temperatureThe reaction mixture was warmed
  3. stirringstirred at 40° to 45° C. for 1 hour
  4. concentrationconcentrated to dryness under reduced pressure
  5. dissolutionThe residue was dissolved in methylene chloride and, upon addition of hexane
  6. customthere was produced insoluble matter, which
  7. filtrationwas filtered out
  8. concentrationThe filtrate was concentrated to dryness under reduced pressure

Sources & evidence

ORD record
ord-c500e8356b4d43b38511d96ae07f3fbb
Source dataset
uspto-grants-1983_10
Patent number
US04409018

Reaction notes

Loading…