Ethanethiol → HCID 21182750, compound

HRID 2163319Notes

Reaction equation

HRID 2163319 reaction equation
[H-].[Na+].[CH3:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[S:12][C:13]3[CH:29]=[CH:28][CH:27]=[CH:26][C:14]=3[C:15]=2[C:16](=[O:25])[C:17]2[CH:22]=[CH:21][C:20]([O:23]C)=[CH:19][CH:18]=2)=[CH:7][CH:6]=1.C(S)C.COC1C=CC(C2SC3C=CC=CC=3C=2CC2C=CC(O)=CC=2)=CC=1>CN(C=O)C>[CH3:3][O:4][C:5]1[CH:6]=[CH:7][C:8]([C:11]2[S:12][C:13]3[CH:29]=[CH:28][CH:27]=[CH:26][C:14]=3[C:15]=2[C:16](=[O:25])[C:17]2[CH:22]=[CH:21][C:20]([OH:23])=[CH:19][CH:18]=2)=[CH:9][CH:10]=1

Participants

6

Reactant 4

HCID 6343EthanethiolHCID 24758Sodium hydrideHCID 10667130HCID 10667130, compoundHCID 22753404HCID 22753404, compound

Product 1

HCID 21182750HCID 21182750, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
70 °C

Procedure

To a suspension of 2.9 g. (0.12 mole) of sodium hydride in oil were added 13 g. (0.035 mole) of 2-(4-methoxyphenyl)-3-(4-methoxybenzoyl)benzothiophene (prepared as in Example 13) dissolved in DMF. The resulting mixture then was added to a cold solution of DMF containing 7.5 g. of ethyl mercaptan. The mixture was stirred at 70° C. for two hours and was monitored by TLC until little or no starting material remained. The total reaction time was about two hours. The mixture then was concentrated to dryness, water was added, and the aqueous mixture was acidified and extracted with ethyl acetate. The ethyl acetate extract was washed, dried over magnesium sulfate, and evaporated to a residue. The residue was recrystallized from benzene to obtain 9.1 g. (73 percent) of 2-(4-methoxyphenyl)-3-(4-hydroxybenzyl)benzothiophene, melting point 188°-189° C.

Workup

  1. additionTo a suspension of 2.9 g
  2. waitThe total reaction time was about two hours
  3. concentrationThe mixture then was concentrated to dryness, water
  4. additionwas added
  5. extractionextracted with ethyl acetate
  6. extractionThe ethyl acetate extract
  7. washwas washed
  8. dry with materialdried over magnesium sulfate
  9. customevaporated to a residue
  10. customThe residue was recrystallized from benzene
  11. customto obtain 9.1 g

Sources & evidence

ORD record
ord-26f8c15ed89b4d59bd5678e7e8753079
Source dataset
uspto-grants-1979_01
Patent number
US04133814

Reaction notes

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