Benzyl mercaptan → HCID 15729535, compound

HRID 846585Notes

Reaction equation

HRID 846585 reaction equation
[CH:1]1[CH:6]=[CH:5][C:4]([CH2:7][SH:8])=[CH:3][CH:2]=1.[H-].[Na+].[F:11][C:12]1[CH:17]=[CH:16][CH:15]=[C:14](F)[N:13]=1>O1CCCC1>[CH2:7]([S:8][C:14]1[CH:15]=[CH:16][CH:17]=[C:12]([F:11])[N:13]=1)[C:4]1[CH:5]=[CH:6][CH:1]=[CH:2][CH:3]=1

Participants

5

Reactant 3

HCID 7509Benzyl mercaptanHCID 24758Sodium hydrideHCID 739342,6-Difluoropyridine

Product 1

HCID 15729535HCID 15729535, compoundYield 74.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

A solution of benzylthiol (5.4 g) in tetrahydrofuran (25 cm3) was added dropwise to a stirred suspension of sodium hydride (1.9 g of a 55% of a dispersion in oil) in tetrahydrofuran (350 cm3) under a nitrogen atmosphere. The mixture was stirred for 30 minutes and a solution of 2,6-difluoropyridine (5 g) in tetrahydrofuran (25 cm3) was added dropwise. The mixture was stirred for a further 3 hours and then carefully quenched with water. The products were extracted into diethyl ether and the combined ether extracts were washed with water and brine solution, then dried over anhydrous magnesium sulphate, filtered and concentrated by evaporation under reduced pressure. The residual dark liquid was purified by chromatography on a silica gel support, eluting with hexane containing 5% by volume ethyl acetate. Fractions containing 15-20 cm3 of eluent were collected separately during the elution, the product being collected in fractions 11 to 19. Evaporation of the eluent gave the title product (7.1 g) as a clear liquid.

Workup

  1. stirringThe mixture was stirred for a further 3 hours
  2. customcarefully quenched with water
  3. extractionThe products were extracted into diethyl ether
  4. washthe combined ether extracts were washed with water and brine solution
  5. dry with materialdried over anhydrous magnesium sulphate
  6. filtrationfiltered
  7. concentrationconcentrated by evaporation under reduced pressure
  8. customThe residual dark liquid was purified by chromatography on a silica gel support
  9. washeluting with hexane containing 5% by volume ethyl acetate
  10. additionFractions containing 15-20 cm3 of eluent
  11. customwere collected separately during the elution
  12. customthe product being collected in fractions 11 to 19
  13. customEvaporation of the eluent

Sources & evidence

ORD record
ord-c02188836f51447caf7b818fe966deff
Source dataset
uspto-grants-1992_08
Patent number
US05137886

Reaction notes

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