Water → HCID 53772381, compound

HRID 1838494Notes

Reaction equation

HRID 1838494 reaction equation
[SH:1][CH2:2][CH2:3][CH2:4][S:5][C:6]1[CH:11]=[CH:10][C:9]([C:12](=[O:25])[C:13]([N:22]([CH3:24])[CH3:23])([CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH3:14])=[CH:8][CH:7]=1.Br[CH2:27][C:28](=[CH2:33])[C:29]([O:31][CH3:32])=[O:30].C(=O)([O-])[O-].[K+].[K+].O>CO>[CH3:32][O:31][C:29](=[O:30])[C:28]([CH2:33][S:1][CH2:2][CH2:3][CH2:4][S:5][C:6]1[CH:11]=[CH:10][C:9]([C:12](=[O:25])[C:13]([N:22]([CH3:23])[CH3:24])([CH3:14])[CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[CH:8][CH:7]=1)=[CH2:27]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 5210932-Propenoic acid, 2-(bromomethyl)-, methyl esterHCID 18755077HCID 18755077, compound

Product 1

HCID 53772381HCID 53772381, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

1.5 g (4.0 mmol) of 1-[4-(3-mercaptopropylthio)phenyl]-2-dimethylamino-2-benzyl-propan-1-one are dissolved in 100 ml of methanol. To the solution are successively added 0.86 g (4.8 mmol) of methyl 2-(bromomethyl)acrylate and 0.55 g (4.0 mmol) of potassium carbonate, and the resulting reaction mixture is stirred at room temperature for 10 min. The reaction mixture is added to water and extracted with ethyl acetate. The organic phase is washed with water, and dried over MgSO4. After distilling off the ethyl acetate, the residue is purified by means of column chromatography on silica gel with ethyl acetate-hexane (1:7) as an eluent, and an oily product is obtained.

Workup

  1. customthe resulting reaction mixture
  2. extractionextracted with ethyl acetate
  3. washThe organic phase is washed with water
  4. dry with materialdried over MgSO4
  5. distillationAfter distilling off the ethyl acetate
  6. customthe residue is purified by means of column chromatography on silica gel with ethyl acetate-hexane (1:7) as an eluent
  7. customan oily product is obtained

Sources & evidence

ORD record
ord-ce4ba7e402ff4919a8b44a43d50ce5b2
Source dataset
uspto-grants-2004_01
Patent number
US06673850B1

Reaction notes

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