Potassium Iodide → HCID 13536190, compound

HRID 652431Notes

Reaction equation

HRID 652431 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[O:12][CH2:11][C:10](=[O:13])[CH:9]([C:14]([O:16][CH3:17])=[O:15])[S:8][C:7]=2[CH:18]=1.Br[CH2:20][CH2:21][CH2:22][Cl:23].C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>[I-].C([N+](CCCC)(CCCC)CCCC)CCC.C(#N)C>[Cl:23][CH2:22][CH2:21][CH2:20][C:9]1([C:14]([O:16][CH3:17])=[O:15])[S:8][C:7]2[CH:18]=[C:3]([O:2][CH3:1])[CH:4]=[CH:5][C:6]=2[O:12][CH2:11][C:10]1=[O:13]

Participants

7

Reactant 4

HCID 4875Potassium IodideHCID 80061-Bromo-3-chloropropaneHCID 11430Potassium CarbonateHCID 13536177HCID 13536177, compound

Product 1

HCID 13536190HCID 13536190, compound

Reagents, catalysts & solvents 2

HCID 67553Tetrabutylammonium IodideCatalystHCID 6342AcetonitrileSolvent

Procedure

A mixture of 30 g of methyl 7-methoxy-3-oxo-3,4-dihydro-2H-1,5-benzoxathiepin-4-carboxylate, 50 g of 1-bromo-3-chloropropane, 46 g of anhydrous potassium carbonate, 10 g of potassium iodide, 1.0 g of tetrabutyl ammonium iodide and 300 ml of acetonitrile is heated under reflux for 4 hours. After the mixture is cooled, the inorganic substance is filtered off, and the filtrate is concentrated under reduced pressure. The resulting residue is dissolved in ethyl acetate, and the solution is washed with water and dried. The solvent is evaporated off under reduced pressure, and the residue is purified by column chromatography on silica gel (eluent:hexane:ethyl acetate:methylene chloride =10:1:10). Recrystallization from ethanol yields colorless prisms of methyl 4-(3-chloropropyl)-7-methoxy-3-oxo-3,4-dihydro-2H-1,5-benzoxathiepin-4-carboxylate. Yield of 17 g. m.p. of 64°-65° C.

Workup

  1. temperatureis heated
  2. temperatureunder reflux for 4 hours
  3. temperatureAfter the mixture is cooled
  4. filtrationthe inorganic substance is filtered off
  5. concentrationthe filtrate is concentrated under reduced pressure
  6. dissolutionThe resulting residue is dissolved in ethyl acetate
  7. washthe solution is washed with water
  8. customdried
  9. customThe solvent is evaporated off under reduced pressure
  10. customthe residue is purified by column chromatography on silica gel (eluent:hexane:ethyl acetate:methylene chloride =10:1:10)
  11. customRecrystallization from ethanol

Sources & evidence

ORD record
ord-7675a0920bd04983876785a39d250730
Source dataset
uspto-grants-1987_06
Patent number
US04672064

Reaction notes

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