Acetonitrile → 7-Chloro-2-{5-[bis(3-methoxycarbonylpropylthio)methyl]-benzofuran-2-yl}quinoline

HRID 2258526Notes

Reaction equation

HRID 2258526 reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][C:8]([C:12]3[O:13][C:14]4[CH:20]=[CH:19][C:18]([CH:21]=O)=[CH:17][C:15]=4[CH:16]=3)=[N:9]2)=[CH:4][CH:3]=1.CN(C)[C:25](=O)[CH2:26][CH2:27][SH:28].[SH:31][CH2:32][CH2:33][CH2:34][C:35]([O:37][CH3:38])=[O:36].[C:39](=[O:42])([O-])[OH:40].[Na+].[C:44](#N)C>B(F)(F)F.CCOCC>[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][C:8]([C:12]3[O:13][C:14]4[CH:20]=[CH:19][C:18]([CH:21]([S:28][CH2:27][CH2:26][CH2:25][C:39]([O:40][CH3:44])=[O:42])[S:31][CH2:32][CH2:33][CH2:34][C:35]([O:37][CH3:38])=[O:36])=[CH:17][C:15]=4[CH:16]=3)=[N:9]2)=[CH:4][CH:3]=1

Participants

7

Reactant 5

HCID 6342AcetonitrileHCID 516892Sodium BicarbonateHCID 11126302Propanamide, 3-mercapto-N,N-dimethyl-HCID 11332495Methyl 4-sulfanylbutanoateHCID 229221457-Chloro-2-(5-formylbenzofuran-2-yl)quinoline

Product 1

HCID 229221607-Chloro-2-{5-[bis(3-methoxycarbonylpropylthio)methyl]-benzofuran-2-yl}quinoline

Reagents, catalysts & solvents 1

HCID 8000Boron trifluoride etherateSolvent

Procedure

To a cooled mixture of 7-chloro-2-(5-formylbenzofuran-2-yl)quinoline (0.77 g), N,N-dimethyl-3-mercaptopropionamide (0.37 g) and methyl 4-mercaptobutyrate (0.37 g) in acetonitrile (15 ml), boron trifluoride etherate (1.38 ml) was added dropwise at 0° C. After being stored in refrigerator for 18 hours, the resulting mixture was poured into ice-water, adjusted to pH 7 with aqueous sodium hydrogen carbonate solution and extracted with diethyl ether. The organic layer was washed with brine, dried over magnesium sulfate and concentrated under reduced pressure to give a mixture containing 3 compounds. The mixture was subjected to column chromatography on silica gel and eluted with toluene, successively a mixture of toluene and ethyl acetate (8:2) and at last a mixture of chloroform and methanol (10:1). The fractions eluted with toluene were concentrated under reduced pressure to give an oil of 7-chloro-2-{5-[bis(3-methoxycarbonylpropylthio)methyl]-benzofuran-2-yl}quinoline (0.25 g).

Workup

  1. additionwas added dropwise at 0° C
  2. extractionextracted with diethyl ether
  3. washThe organic layer was washed with brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customto give a mixture
  7. additioncontaining 3 compounds
  8. washeluted with toluene
  9. additionsuccessively a mixture of toluene and ethyl acetate (8:2)
  10. additionat last a mixture of chloroform and methanol (10:1)
  11. washThe fractions eluted with toluene
  12. concentrationwere concentrated under reduced pressure

Sources & evidence

ORD record
ord-adbc85c0912d4431b5f69b891857364d
Source dataset
uspto-grants-1997_08
Patent number
US05661159

Reaction notes

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