Potassium Carbonate → HCID 178498982, compound

HRID 274859Notes

Reaction equation

HRID 274859 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-64d8885a3fda46b49776d15c2f1870fb
Source dataset
uspto-grants-1995_02
Patent number
US05391540

Reaction notes

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