Dimethylcarbamoyl Chloride → HCID 66786079, compound

HRID 1615083Notes

Reaction equation

HRID 1615083 reaction equation
[Si:1]([O:8][CH2:9][CH:10]([CH2:21][O:22][Si:23]([C:26]([CH3:29])([CH3:28])[CH3:27])([CH3:25])[CH3:24])[CH2:11][CH2:12][CH2:13][C:14]1[CH:19]=[CH:18][N+:17]([O-])=[CH:16][CH:15]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].C[Si]([C:34]#[N:35])(C)C.CN(C)C(Cl)=O.C([O-])(O)=O.[Na+]>C(Cl)(Cl)Cl>[Si:1]([O:8][CH2:9][CH:10]([CH2:21][O:22][Si:23]([C:26]([CH3:29])([CH3:28])[CH3:27])([CH3:25])[CH3:24])[CH2:11][CH2:12][CH2:13][C:14]1[CH:19]=[CH:18][N:17]=[C:16]([C:34]#[N:35])[CH:15]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 6598Dimethylcarbamoyl ChlorideHCID 82115Trimethylsilyl cyanideHCID 516892Sodium BicarbonateHCID 66785983HCID 66785983, compound2×

Product 1

HCID 66786079HCID 66786079, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of the crude 4-[5-(tert-butyldimethylsilanyloxy)-4-(tert-butyldimethylsilanyloxy-methyl)-pentyl]pyridine 1-oxide (0.43 g) prepared in (5) in chloroform (5 mL) were added trimethylsilyl cyanide (0.17 mL) and N,N-dimethylcarbamoyl chloride (0.12 mL). The reaction mixture was stirred at RT for 12 hr. Saturated aqueous NaHCO3 was added to the reaction mixture and the mixture was extracted with chloroform. The organic layer was dried over Na2SO4. The solvent was removed under reduced pressure. The residue was purified by silica gel chromatography (Developing solvent: hexane/ethyl acetate=9/1) to give the title compound (0.40 g, 87%).

Workup

  1. extractionthe mixture was extracted with chloroform
  2. dry with materialThe organic layer was dried over Na2SO4
  3. customThe solvent was removed under reduced pressure
  4. customThe residue was purified by silica gel chromatography (Developing solvent: hexane/ethyl acetate=9/1)

Sources & evidence

ORD record
ord-0a946f2b0c534b6d9d85e993ec8f6d99
Source dataset
uspto-grants-2014_07
Patent number
US08765739B2

Reaction notes

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