HCID 13066692, compound → HCID 13066717, compound

HRID 1164091Notes

Reaction equation

HRID 1164091 reaction equation
[C:1]([C:3]([C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([S:16]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=2[Cl:25])(=[O:18])=[O:17])[C:11]=1OC)(C)[C:4]([O:6]CC)=[O:5])#N>I.C(O)(=O)C>[CH3:1][CH:3]1[C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([S:16]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=3[Cl:25])(=[O:18])=[O:17])[C:11]=2[O:6][C:4]1=[O:5]

Participants

4

Reactant 1

HCID 13066692HCID 13066692, compound

Product 1

HCID 13066717HCID 13066717, compoundYield 77.2%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 24841Hydrogen iodideSolvent

Procedure

A solution of ethyl 2-cyano-2-[2-methoxy-3-(2-chlorobenzenesulfonyl)phenyl]propionate (3.6 g) in hydriodic acid (58%, 10 ml) and glacial acetic acid (30 ml) was refluxed under heating for 21 hours. After cooling, the reaction mixture was concentrated under reduced pressure. To the residue was added dil. aqueous sodium hydrogen sulfite, and the mixture was extracted with diethyl ether. The extract was washed with dil. aqueous sodium hydrogen sulfite and water in turn, dried and evaporated under reduced pressure. To the oily residue was added acetic anhydride (5 ml), and the mixture was refluxed under heating for 10 minutes and then evaporated under reduced pressure. The resultant residue was crystallized with ethanol to give 3-methyl-7-(2-chlorobenzenesulfonyl)-2,3-dihydrobenzofuran-2-one (2.2 g), mp. 94°-96° C.

Workup

  1. temperatureunder heating for 21 hours
  2. temperatureAfter cooling
  3. concentrationthe reaction mixture was concentrated under reduced pressure
  4. additionTo the residue was added dil. aqueous sodium hydrogen sulfite
  5. extractionthe mixture was extracted with diethyl ether
  6. washThe extract was washed with dil. aqueous sodium hydrogen sulfite and water in turn
  7. customdried
  8. customevaporated under reduced pressure
  9. additionTo the oily residue was added acetic anhydride (5 ml)
  10. temperaturethe mixture was refluxed
  11. temperatureunder heating for 10 minutes
  12. customevaporated under reduced pressure
  13. customThe resultant residue was crystallized with ethanol

Sources & evidence

ORD record
ord-71a8cd731c594d81b9636d8cec4d5a38
Source dataset
uspto-grants-1983_01
Patent number
US04367238

Reaction notes

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