Dimethylamine → 2-benzyloxy-N,N-dimethyl-5-vinylbenzamide

HRID 1862626Notes

Reaction equation

HRID 1862626 reaction equation
[CH2:1]([O:8][C:9]1[CH:17]=[CH:16][C:15]([CH:18]=[CH2:19])=[CH:14][C:10]=1[C:11](O)=[O:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.S(Cl)(Cl)=O.[CH3:24][N:25](C)[CH:26]=O.CNC>C1C=CC=CC=1.O1CCCC1.O>[CH2:1]([O:8][C:9]1[CH:17]=[CH:16][C:15]([CH:18]=[CH2:19])=[CH:14][C:10]=1[C:11]([N:25]([CH3:26])[CH3:24])=[O:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

8

Reactant 4

HCID 674DimethylamineHCID 6228DimethylformamideHCID 24386Thionyl ChlorideHCID 18620158HCID 18620158, compound

Product 1

HCID 186201442-benzyloxy-N,N-dimethyl-5-vinylbenzamide

Reagents, catalysts & solvents 3

HCID 241BenzeneSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-benzyloxy-5-vinylbenzoic acid (607 mg) in benzene (10 ml) were added thionyl chloride (350 μl) and a catalytic amount of N,N-dimethylformamide, and the mixture was heated under reflux for 1 hour with stirring. After concentration of the reaction mixture under reduced pressure, the residue was dissolved in tetrahydrofuran (5 ml), and an excess amount of 50% aqueous dimethylamine solution was added to the stirred solution under ice-cooling. Water was added to the reaction mixture, and the resulting mixture was extracted with ethyl acetate. The extract was washed with brine and dried over anhydrous magnesium sulfate. After the solvent was removed under reduced pressure, purification of the residue by flash column chromatography on silica gel (eluent:hexane/diethyl ether/dichloromethane=1/2/2) gave 2-benzyloxy-N,N-dimethyl-5-vinylbenzamide (548 mg).

Workup

  1. temperatureunder reflux for 1 hour
  2. temperaturecooling
  3. extractionthe resulting mixture was extracted with ethyl acetate
  4. washThe extract was washed with brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customAfter the solvent was removed under reduced pressure, purification of the residue by flash column chromatography on silica gel (eluent:hexane/diethyl ether/dichloromethane=1/2/2)

Sources & evidence

ORD record
ord-d7b3e1182759471c8e169d4f7c85d238
Source dataset
uspto-grants-2003_03
Patent number
US06538152B1

Reaction notes

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