Dichloromethane → HCID 14718735, compound

HRID 1085704Notes

Reaction equation

HRID 1085704 reaction equation
Cl[CH:2]([C:7]1[CH:8]=[N:9][C:10]([C:13]([CH3:16])([CH3:15])[CH3:14])=[N:11][CH:12]=1)[C:3]([CH3:6])([CH3:5])[CH3:4].[C-:17]#[N:18].[Na+].C(=O)(O)[O-].[Na+].ClCCl>CS(C)=O.C(OCC)(=O)C>[CH3:4][C:3]([CH3:6])([CH3:5])[CH:2]([C:7]1[CH:8]=[N:9][C:10]([C:13]([CH3:16])([CH3:15])[CH3:14])=[N:11][CH:12]=1)[C:17]#[N:18]

Participants

7

Reactant 4

HCID 6344Dichloromethane2×HCID 8929Sodium CyanideHCID 516892Sodium BicarbonateHCID 14718736HCID 14718736, compound

Product 1

HCID 14718735HCID 14718735, compoundYield 155.7%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 1-chloro-2,2-dimethyl-1-[2-(1,1-dimethylethyl)pyrimidin-5-yl]propane (5.08 g) and sodium cyanide (2.07 g) in dry dimethylsulphoxide (50 cm3) was heated to 60° C., under an atmosphere of dry nitrogen for a period of 17 hours. After cooling to the ambient temperature, the solution was poured into aqueous sodium bicarbonate solution and extracted with diethyl ether, washed with brine, dried over anhydrous magnesium sulphate, and concentrated by evaporation of the solvent under reduced pressure. The resulting brown oil was combined with the crude product from a similar reaction and subjected to column chromatography on silica gel using dichloromethane followed by dichloromethane containing 5% by volume ethyl acetate to give 3,3-dimethyl-2-[2-(1,1-dimethylethyl)pyrimidin-5-yl]butyronitrile (7.6 g), identical in all respects to the material obtained in Example 15 (ii) above.

Workup

  1. extractionextracted with diethyl ether
  2. washwashed with brine
  3. dry with materialdried over anhydrous magnesium sulphate
  4. concentrationconcentrated by evaporation of the solvent under reduced pressure
  5. customThe resulting brown oil was combined with the crude product from a similar reaction

Sources & evidence

ORD record
ord-289907db6cbb4d9bad3f83a458548ff9
Source dataset
uspto-grants-1991_04
Patent number
US05010200

Reaction notes

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