Ethanethiol → 2-(4-Methoxyphenyl)-3-(4-Hydroxybenzoyl)-6-Methoxybenzo[b]thiophene

HRID 2185969Notes

Reaction equation

HRID 2185969 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[S:13][C:12]3[CH:14]=[C:15]([O:18][CH3:19])[CH:16]=[CH:17][C:11]=3[C:10]=2[C:20](=[O:29])[C:21]2[CH:26]=[CH:25][C:24]([O:27]C)=[CH:23][CH:22]=2)=[CH:5][CH:4]=1.[H-].[Na+].C(S)C>CN(C)C=O>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([C:9]2[S:13][C:12]3[CH:14]=[C:15]([O:18][CH3:19])[CH:16]=[CH:17][C:11]=3[C:10]=2[C:20](=[O:29])[C:21]2[CH:22]=[CH:23][C:24]([OH:27])=[CH:25][CH:26]=2)=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 6343EthanethiolHCID 24758Sodium hydrideHCID 9953060LY88074 Trimethyl ether

Product 1

HCID 98651972-(4-Methoxyphenyl)-3-(4-Hydroxybenzoyl)-6-Methoxybenzo[b]thiopheneYield 55.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2-(4-Methoxyphenyl)-3-(4-Methoxybenzoyl)-6-Methoxybenzo[b]thiophene (19.8 g, 49 mmol) was dissolved in dimethylformamide and sodium hydride (10 g of a 50% oil dispersion) was added. The reaction was cooled and ethylmercaptan (12.4 g) was added slowly. The reaction was warmed to 65° C.-70° C. until the reaction was complete. The volatiles were removed by evaporation, water was added to the reaction mixture, and the resulting mixture was extracted with ethyl acetate. The ethyl acetate extracts were washed with water and evaporated to dryness. The residue was chromatographed on a silica gel column eluting with 1500 mL of benzene-ethyl acetate (99:1), then benzene-ethyl acetate (97:3). The fractions containing the title compound were evaporated to dryness and the residue was crystallized from benzene to give 10.7 g of the title compound. mp 114° C.-116° C. EA calculated for C23H18O4S: C, 70.75; H, 4.64; O, 16.39. Found: C, 70.88; H, 4.50; O, 16.11.

Workup

  1. temperatureThe reaction was cooled
  2. temperatureThe reaction was warmed to 65° C.-70° C. until the reaction
  3. customThe volatiles were removed by evaporation, water
  4. additionwas added to the reaction mixture
  5. extractionthe resulting mixture was extracted with ethyl acetate
  6. washThe ethyl acetate extracts were washed with water
  7. customevaporated to dryness
  8. customThe residue was chromatographed on a silica gel column
  9. washeluting with 1500 mL of benzene-ethyl acetate (99:1)
  10. additionThe fractions containing the title compound
  11. customwere evaporated to dryness
  12. customthe residue was crystallized from benzene

Sources & evidence

ORD record
ord-dfabc2bd1a2e4005889666f4a53b4e0b
Source dataset
uspto-grants-2002_06
Patent number
US06403615B1

Reaction notes

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