N,N-Dimethylaniline → HCID 15725053, compound

HRID 846677Notes

Reaction equation

HRID 846677 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[C:2]1[S:10][C:11]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)([CH3:14])[CH2:12][OH:13].CN(C)C1C=CC=CC=1.[C:30](Cl)(=[O:32])[CH3:31]>CN(C=O)C.O>[C:30]([O:13][CH2:12][C:11]([S:10][C:2]1[NH:1][C:9]2[C:4]([CH:3]=1)=[CH:5][CH:6]=[CH:7][CH:8]=2)([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[CH3:14])(=[O:32])[CH3:31]

Participants

6

Reactant 3

HCID 949N,N-DimethylanilineHCID 6367Acetyl chlorideHCID 15725052HCID 15725052, compound

Product 1

HCID 15725053HCID 15725053, compoundYield 42%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Procedure

To a solution (20 ml) of 2-(1H-indol-2-yl)thio-2-phenylpropanol (2.81 g) and N,N-dimethylaniline (1.23 g) in anhydrous DMF, was a solution (2 ml) of acetyl chloride (0.86 g) in anhydrous DMF was added dropwise. The mixture was stirred at room temperature overnight. The reaction solution was diluted with water, and was extracted with ethyl acetate. The organic layer was washed with 1N hydrochloric acid, water, and a saturated aqueous sodium chloride solution, and was dried over anhydrous sodium sulfate. The solvent was evaporated off under reduced pressure. The residue was purified by silica gel column chromatography (diluting solvent: n-hexane/ethyl acetate =9:1), and further recrystallized from ethanol to give 1.35 g (yield: 42 %) of the product compound as a pale yellow prism crystal. The melting point was 105°-106° C.

Workup

  1. additionwas added dropwise
  2. extractionwas extracted with ethyl acetate
  3. washThe organic layer was washed with 1N hydrochloric acid, water
  4. dry with materiala saturated aqueous sodium chloride solution, and was dried over anhydrous sodium sulfate
  5. customThe solvent was evaporated off under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (diluting solvent: n-hexane/ethyl acetate =9:1)
  7. customfurther recrystallized from ethanol

Sources & evidence

ORD record
ord-919889f72b5c44dab6e2ca8d7fc49545
Source dataset
uspto-grants-1992_08
Patent number
US05137909

Reaction notes

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