Water → (4-Methoxyphenyl)[5-[(phenylmethyl)thio]-2-thienyl]methanone

HRID 1153787Notes

Reaction equation

HRID 1153787 reaction equation
[CH2:1]([SH:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].Br[C:12]1[S:13][C:14]([C:17](=[O:26])[C:18]2[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[CH:20][CH:19]=2)=[CH:15][CH:16]=1.O>CN(C=O)C>[CH2:1]([S:8][C:12]1[S:13][C:14]([C:17](=[O:26])[C:18]2[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[CH:20][CH:19]=2)=[CH:15][CH:16]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7509Benzyl mercaptanHCID 24758Sodium hydrideHCID 298606Methanone, (5-bromo-2-thienyl)(4-methoxyphenyl)-

Product 1

HCID 13364599(4-Methoxyphenyl)[5-[(phenylmethyl)thio]-2-thienyl]methanone

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
25 °C

Procedure

Benzyl mercaptan (1.24 g, 0.01 mol) was added to a stirred mixture of sodium hydride (50% oil dispersion, 0.44 g, 0.11 mol) and degassed DMF (10 mL). The resulting mixture was warmed cautiously until gas evolution ceased. After cooling to 25° C., a solution of 2-bromo-5-(4-methoxybenzoyl)thiophene (2.97 g, 0.01 mol) in DMF (10 mL) was added dropwise. After complete addition, the mixture was heated on the steam bath for 2.5 hours and poured into waTER (200 mL). The aqueous mixture was extracted with ether (2×200 mL) and the extracts were washed with water, saturated NaCl solution and dried (Na2SO4). After evaporation of the solvent, the residue was collected with the aid of hexane and dried, 1.98 g, m.p. 103°-105° C.

Workup

  1. customdegassed DMF (10 mL)
  2. temperatureThe resulting mixture was warmed cautiously until gas evolution
  3. additionAfter complete addition
  4. temperaturethe mixture was heated on the steam bath for 2.5 hours
  5. extractionThe aqueous mixture was extracted with ether (2×200 mL)
  6. washthe extracts were washed with water, saturated NaCl solution
  7. dry with materialdried (Na2SO4)
  8. customAfter evaporation of the solvent
  9. customthe residue was collected with the aid of hexane
  10. customdried

Sources & evidence

ORD record
ord-f1d6fc5116004de9b68c5f6380bbb4e5
Source dataset
uspto-grants-1984_12
Patent number
US04486444

Reaction notes

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