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

HRID 1702120Notes

Reaction equation

HRID 1702120 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 with stirring over a 20-minute period. The reaction solution 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 the insoluble matter resulting from the addition of hexane was filtered out. The filtrate was concentrated to dryness under reduced pressure, thereby producing 19.5 g (yield of 87%) of the subject compound as crystals. Recrystallization from cyclohexane yielded white crystals, m.p. 89°-90° C.

Workup

  1. additionwas added to the suspension
  2. temperatureThe reaction solution 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
  6. customthe insoluble matter resulting from the addition of hexane
  7. filtrationwas filtered out
  8. concentrationThe filtrate was concentrated to dryness under reduced pressure

Sources & evidence

ORD record
ord-fa6ea2de4da94fa6992c5665d69f92e0
Source dataset
uspto-grants-1983_04
Patent number
US04380466

Reaction notes

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