Ethanethiol → HCID 20528832, compound

HRID 67205Notes

Reaction equation

HRID 67205 reaction equation
C(S)C.C[O:5][C:6]1[CH:11]=[CH:10][C:9]([CH2:12][CH2:13][CH:14]([CH2:19][C:20]([OH:22])=[O:21])[CH2:15][C:16]([OH:18])=[O:17])=[CH:8][CH:7]=1>CN(C)C=O>[OH:5][C:6]1[CH:11]=[CH:10][C:9]([CH2:12][CH2:13][CH:14]([CH2:15][C:16]([OH:18])=[O:17])[CH2:19][C:20]([OH:22])=[O:21])=[CH:8][CH:7]=1

Participants

4

Reactant 2

HCID 6343EthanethiolHCID 20528830HCID 20528830, compound

Product 1

HCID 20528832HCID 20528832, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a suspension of 57% sodium hydride-paraffin (2.2 g) in dry dimethylformamide (70 ml) in an atmosphere of nitrogen is slowly added ethanethiol (4.0 ml). The mixture is stirred at room temperature until a clear solution results. To this solution is added a solution of 3-[2-(4-methoxyphenyl)ethyl]glutaric acid (1.2 g) in dry dimethylformamide (10 ml) and the mixture is heated with stirring in a bath at 165° C. for 6.0 hours. The mixture is then evaporated to dryness in vacuo and the resulting residue is dissolved in water (50 ml), extracted with ether (two 50 ml portions) and the ether extract is discarded. The aqueous solution is acidified with concentrated hydrochloric acid and extracted with ethyl acetate. The ethyl acetate solution is washed with brine, dried with anhydrous magnesium sulfate, and evaporated to a residue. Crystallization of this from chloroform-hexane affords 1.0 g of the title compound, melting point 142°-144° C.

Workup

  1. customresults
  2. temperaturethe mixture is heated
  3. stirringwith stirring in a bath at 165° C. for 6.0 hours
  4. customThe mixture is then evaporated to dryness in vacuo
  5. dissolutionthe resulting residue is dissolved in water (50 ml)
  6. extractionextracted with ether (two 50 ml portions)
  7. extractionthe ether extract
  8. extractionextracted with ethyl acetate
  9. washThe ethyl acetate solution is washed with brine
  10. dry with materialdried with anhydrous magnesium sulfate
  11. customevaporated to a residue
  12. customCrystallization of this from chloroform-hexane

Sources & evidence

ORD record
ord-30e6fd5ebf134c2daef4ab693d435e4f
Source dataset
uspto-grants-1982_08
Patent number
US04345096

Reaction notes

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