Sodium Chloride → 3-ACETYLPHENYLDIMETHYLCARBAMATE

HRID 1785341Notes

Reaction equation

HRID 1785341 reaction equation
[H-].[Na+].[OH:3][C:4]1[CH:5]=[C:6]([C:10](=[O:12])[CH3:11])[CH:7]=[CH:8][CH:9]=1.[CH3:13][N:14]([CH3:18])[C:15](Cl)=[O:16].[Cl-].[Na+]>O1CCCC1>[CH3:13][N:14]([CH3:18])[C:15](=[O:16])[O:3][C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([C:10](=[O:12])[CH3:11])[CH:5]=1

Participants

6

Reactant 4

HCID 5234Sodium ChlorideHCID 6598Dimethylcarbamoyl ChlorideHCID 84873-HydroxyacetophenoneHCID 24758Sodium hydride

Product 1

HCID 216800743-ACETYLPHENYLDIMETHYLCARBAMATEYield 166.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Tetrahydrofuran (100 ml) was added to sodium hydride (1.94 g, 45 mmol) under an atmosphere of nitrogen. To the suspension was added a tetrahydrofuran solution of 1-(3-hydroxyphenyl)ethanone (5.05 g, 37 mmol) in an ice bath. After stirring the mixture for 15 minutes dimethylcarbamyl chloride (1.7 ml, 19 mmol) was added dropwise into the mixture and the resulting mixture was stirred at room temperature for 4 hours. Saturated aqueous sodium chloride solution was added to the reaction mixture. The resulting mixture was extracted with ethyl acetate. The organic layer was washed with water and saturated sodium chloride solution, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by chromatography on a silica gel column to afford the desired compound (6.54 g).

Workup

  1. additionwas added dropwise into the mixture
  2. extractionThe resulting mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with water and saturated sodium chloride solution
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by chromatography on a silica gel column

Sources & evidence

ORD record
ord-4ef83791b27440f6aed4244de8eb74e9
Source dataset
uspto-grants-2009_03
Patent number
US07504437B2

Reaction notes

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