Acetonitrile → 4-Tert-butyl-2-{5-[bis-(3-methoxycarbonylpropylthio)methyl]benzofuran-2-yl}thiazole

HRID 487687Notes

Reaction equation

HRID 487687 reaction equation
[C:1]([C:5]1[N:6]=[C:7]([C:10]2[O:11][C:12]3[CH:18]=[CH:17][C:16]([CH:19]=O)=[CH:15][C:13]=3[CH:14]=2)[S:8][CH:9]=1)([CH3:4])([CH3:3])[CH3:2].CN(C)[C:23](=O)[CH2:24][CH2:25][SH:26].[SH:29][CH2:30][CH2:31][CH2:32][C:33]([O:35][CH3:36])=[O:34].[C:37](=[O:40])([O-])[OH:38].[Na+].[C:42](#N)C>B(F)(F)F.CCOCC>[C:1]([C:5]1[N:6]=[C:7]([C:10]2[O:11][C:12]3[CH:18]=[CH:17][C:16]([CH:19]([S:26][CH2:25][CH2:24][CH2:23][C:37]([O:38][CH3:42])=[O:40])[S:29][CH2:30][CH2:31][CH2:32][C:33]([O:35][CH3:36])=[O:34])=[CH:15][C:13]=3[CH:14]=2)[S:8][CH:9]=1)([CH3:2])([CH3:4])[CH3:3]

Participants

7

Reactant 5

HCID 6342AcetonitrileHCID 516892Sodium BicarbonateHCID 11126302Propanamide, 3-mercapto-N,N-dimethyl-HCID 11332495Methyl 4-sulfanylbutanoateHCID 196038064-Tert-butyl-2-(5-formylbenzofuran-2-yl)thiazole

Product 1

HCID 190927024-Tert-butyl-2-{5-[bis-(3-methoxycarbonylpropylthio)methyl]benzofuran-2-yl}thiazole

Reagents, catalysts & solvents 1

HCID 8000Boron trifluoride etherateSolvent

Procedure

To a cooled mixture of 4-tert-butyl-2-(5-formylbenzofuran-2-yl)thiazole (0.713 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 (20:1 to 3:1) 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 4-tert-butyl-2-{5-[bis-(3-methoxycarbonylpropylthio)methyl]benzofuran-2-yl}thiazole (0.3 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 (20:1 to 3:1)
  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-0b5a498ba62b40d1a6441978c8f1875f
Source dataset
uspto-grants-1994_03
Patent number
US05296495

Reaction notes

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