Acetic Anhydride → HCID 13257591, compound

HRID 647402Notes

Reaction equation

HRID 647402 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:16](=[O:17])[C:15]3(O)[CH:10]([CH2:11][CH2:12][CH2:13][CH2:14]3)[C:9]2=[S:19])=[C:4]([F:20])[CH:3]=1.C(OC(=O)C)(=O)C>N1C=CC=CC=1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:9](=[S:19])[C:10]3[CH2:11][CH2:12][CH2:13][CH2:14][C:15]=3[C:16]2=[O:17])=[C:4]([F:20])[CH:3]=1

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 13252412HCID 13252412, compound

Product 1

HCID 13257591HCID 13257591, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

In 75 ml of pyridine was dissolved 28.2 g of 2-(4-chloro-2-fluorophenyl)-3a-hydroxy-1-thioxo-octahydroisoindole-3-one, and 30 ml of acetic acid anhydride was added to the solution, which was allowed to stand at room temperature overnight. The reaction mixture was concentrated under reduced pressure, and the residue was dissolved in dichloromethane, washed with water and dried over anhydrous sodium sulfate. After distilling off the dichloromethane, the resulting crystals were washed with a small amount of cold ethanol and dried, thereby affording 25.2 g (yield of 95%) of the subject compound. Recrystallization from ethanol yielded red-purple crystals, m.p. 101°-102° C.

Workup

  1. additionwas added to the solution, which
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. dissolutionthe residue was dissolved in dichloromethane
  4. washwashed with water
  5. dry with materialdried over anhydrous sodium sulfate
  6. distillationAfter distilling off the dichloromethane
  7. washthe resulting crystals were washed with a small amount of cold ethanol
  8. customdried

Sources & evidence

ORD record
ord-a96de7086dae4de6bb69246851ce0562
Source dataset
uspto-grants-1983_10
Patent number
US04409018

Reaction notes

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