Triethylamine → 4-(3-Ethoxy-2-hydroxypropoxy)phenylcarbamoylmethyl methyl sulfide

HRID 637531Notes

Reaction equation

HRID 637531 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][C:26](Cl)=[O:27]>CN(C)C=O>[CH3:23][S:24][CH2:25][C:26](=[O:27])[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 111262562-(Methylsulfanyl)acetyl chloride

Product 1

HCID 133860734-(3-Ethoxy-2-hydroxypropoxy)phenylcarbamoylmethyl methyl sulfideYield 95.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Dissolved in 4 ml of dimethylformamide were 2.00 g of triethylamine and 2.11 g of 4-(3-ethoxy-2-hydroxypropoxy)aniline. To the solution was added 1.25 g of methylmercaptoacetyl chloride with ice-cooling and the mixture was stirred at room temperature for 12 hours. The reaction mixture was concentrated and the residue was extracted with chloroform. The chloroform layer was washed with water and concentrated. The resulting residue was purified by silica gel column chromatography using a 1:5 ethanol-chloroform mixture, giving 2.85 g of 4-(3-ethoxy-2-hydroxypropoxy)phenylcarbamoylmethyl methyl sulfide in 95.3% yield.

Workup

  1. temperaturecooling
  2. concentrationThe reaction mixture was concentrated
  3. extractionthe residue was extracted with chloroform
  4. washThe chloroform layer was washed with water
  5. concentrationconcentrated
  6. customThe resulting residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-8a22fcf10aea48389dc7633831772e6a
Source dataset
uspto-grants-1985_12
Patent number
US04556737

Reaction notes

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