Dimethylcarbamoyl Chloride → HCID 67163729, compound

HRID 552488Notes

Reaction equation

HRID 552488 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][N+:11]([O-])=[C:10]([CH3:15])[CH:9]=2)=[CH:4][CH:3]=1.C[Si]([C:20]#[N:21])(C)C.CN(C)C(Cl)=O.C(=O)([O-])[O-].[Na+].[Na+]>C(Cl)Cl>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:9]=[C:10]([CH3:15])[N:11]=[C:12]([C:20]#[N:21])[CH:13]=2)=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 6598Dimethylcarbamoyl ChlorideHCID 10340Sodium CarbonateHCID 82115Trimethylsilyl cyanideHCID 67163938HCID 67163938, compound

Product 1

HCID 67163729HCID 67163729, compoundYield 162%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1.30 g (6.4 mmol) of 4-(4-Fluoro-phenyl)-2-methyl-pyridine 1-oxide in 20 ml of methylene chloride was added dropwise 1.00 ml (8.0 mmol, 1.25 equiv.) of Trimethylsilyl cyanide. Then 0.73 ml (0.86 g, 8.0 mmol, 1.25 equiv.) of Dimethylcarbamoyl chloride was added dropwise over a period of 5 min. After stirring overnight at room temperature, 8 ml of saturated sodium carbonate solution were added. The aqueous phase was extracted twice with 15 ml of methylene chloride. The combined organic phases were washed with 20 ml of brine, dried over magnesium sulfate, and concentrated in vaccuo to yield 2.2 g of a beige solid which was purified by flash chromatography (ethyl acetate/hexane 1:4) to yield the title compound (0.75 g, 55%) as a crystalline white solid, MS (ISP): m/e=213.1 (M+H)+.

Workup

  1. extractionThe aqueous phase was extracted twice with 15 ml of methylene chloride
  2. washThe combined organic phases were washed with 20 ml of brine
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated in vaccuo

Sources & evidence

ORD record
ord-845f1456049b4363903157687b92eff7
Source dataset
uspto-grants-2011_05
Patent number
US07951824B2

Reaction notes

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