Triethylamine → 2-{4-(3-Ethoxy-2-hydroxypropoxy)phenylcarbamoyl}ethyl methyl sulfide

HRID 637532Notes

Reaction equation

HRID 637532 reaction equation
C(N(CC)CC)C.[CH2:8]([O:10][CH2:11][CH:12]([OH:22])[CH2:13][O:14][C:15]1[CH:21]=[CH:20][C:18]([NH2:19])=[CH:17][CH:16]=1)[CH3:9].[CH3:23][S:24][CH2:25][CH2:26][C:27](Cl)=[O:28]>CN(C)C=O>[CH3:23][S:24][CH2:25][CH2:26][C:27](=[O:28])[NH:19][C:18]1[CH:17]=[CH:16][C:15]([O:14][CH2:13][CH:12]([OH:22])[CH2:11][O:10][CH2:8][CH3:9])=[CH:21][CH:20]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 107748571-(4-Aminophenoxy)-3-ethoxypropan-2-olHCID 129214403-(Methylthio)propionyl Chloride

Product 1

HCID 105912962-{4-(3-Ethoxy-2-hydroxypropoxy)phenylcarbamoyl}ethyl methyl sulfide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Dissolved in 4 ml of dimethylformamide were 1.46 g of triethylamine and 1.52 g of 4-(3-ethoxy-2-hydroxypropoxy)aniline. A 1.10 g quantity of 3-methylmercaptopropionyl chloride was added to the solution with ice-cooling. The mixture was stirred at room temperature for 12 hours and the reaction mixture was concentrated. The residue was extracted with chloroform and the chloroform layer was washed successively with 1N hydrochloric acid, a saturated aqueous solution of sodium hydrogencarbonate and water and concentrated. Ether was added to the residue and the crystals formed were filtered off to give 1.52 g of 2-{4-(3-ethoxy-2-hydroxypropoxy)phenylcarbamoyl}ethyl methyl sulfide in 67.4%, M.P. 79° to 81° C.

Workup

  1. temperaturecooling
  2. concentrationthe reaction mixture was concentrated
  3. extractionThe residue was extracted with chloroform
  4. washthe chloroform layer was washed successively with 1N hydrochloric acid
  5. concentrationa saturated aqueous solution of sodium hydrogencarbonate and water and concentrated
  6. additionEther was added to the residue
  7. customthe crystals formed
  8. filtrationwere filtered off

Sources & evidence

ORD record
ord-f8d0eb0abaaa49c7844a183232104acf
Source dataset
uspto-grants-1985_12
Patent number
US04556737

Reaction notes

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