Potassium Carbonate → HCID 178498982, compound

HRID 1721589Notes

Reaction equation

HRID 1721589 reaction equation
C(C[O:4][C:5]1[C:10]([C:11]([O:13][CH3:14])=[O:12])=[C:9]([CH2:15][CH:16]([CH3:18])[CH3:17])[C:8]([C:19]([O:21][CH3:22])=[O:20])=[C:7]([C:23]([F:26])([F:25])[F:24])[N:6]=1)#N.BrCC#N.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[OH:4][C:5]1[C:10]([C:11]([O:13][CH3:14])=[O:12])=[C:9]([CH2:15][CH:16]([CH3:18])[CH3:17])[C:8]([C:19]([O:21][CH3:22])=[O:20])=[C:7]([C:23]([F:25])([F:24])[F:26])[N:6]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 11534BromoacetonitrileHCID 57319209HCID 57319209, compound

Product 1

HCID 178498982HCID 178498982, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

This example illustrates the preparation of Compound 80, namely, dimethyl 2-(cyanomethoxy)-4-(2-methylpropyl)-6-(trifluoromethyl)-3,5-pyridine-dicarboxylate. A solution of 6.38 g (0.019 mol) of dimethyl 2-hydroxy-4-(2-methylpropyl)-6-(trifluoromethyl)-3,5-pyridinedicarboxylate (Compound 1) in 50 mL of dimethylformamide was prepared and to it was added 7.2 g (0.06 mol) of bromoacetonitrile and 8.3 g (0.06 mol) of anhydrous potassium carbonate. The mixture was stirred at room temperature overnight then suction filtered. The filtrate was diluted with 400 mL of water and extracted with four 50 mL portions of methylene chloride. The combined extracts were dried with magnesium sulfate and the solvent was removed by rotary evaporation giving 7.09 g (98.9% yield) of a dark amber oil. Silica gel chromatography with 10% ethyl acetate, 90% cyclohexane gave 3.51 g (49%) of Compound 80 as a clear colorless oil.

Workup

  1. filtrationsuction filtered
  2. additionThe filtrate was diluted with 400 mL of water
  3. extractionextracted with four 50 mL portions of methylene chloride
  4. dry with materialThe combined extracts were dried with magnesium sulfate
  5. customthe solvent was removed by rotary evaporation

Sources & evidence

ORD record
ord-bd5fbed7334e4ba9a4bc577d849df22f
Source dataset
uspto-grants-1996_04
Patent number
US05512536

Reaction notes

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