Potassium Cyanide → HCID 18374266, compound

HRID 2300029Notes

Reaction equation

HRID 2300029 reaction equation
CS([C:5]1[N:10]=[C:9]([C:11]([F:14])([F:13])[F:12])[C:8]([C:15]([O:17][CH2:18][CH3:19])=[O:16])=[CH:7][CH:6]=1)(=O)=O.[C-:20]#[N:21].[K+].C1OCCOCCOCCOCCOCCOC1>CN(C)C=O>[C:20]([C:5]1[N:10]=[C:9]([C:11]([F:14])([F:13])[F:12])[C:8]([C:15]([O:17][CH2:18][CH3:19])=[O:16])=[CH:7][CH:6]=1)#[N:21]

Participants

5

Reactant 3

HCID 9032Potassium Cyanide2×HCID 2855718-Crown-6HCID 18374279HCID 18374279, compound

Product 1

HCID 18374266HCID 18374266, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Under an atmosphere of nitrogen and with stirring, a solution of 0.596 g of ethyl 6-methylsulfonyl-2-trifluoromethylpyridin-3-ylcarboxylate in 5 ml of dimethylformamide is treated with 160 mg of solid potassium cyanide and a spatula tipful of 18-crown-6, and the mixture is heated at 80° C. for 3 hours. The mixture is cooled overnight, and the next day another 30 mg of potassium cyanide are added and the mixture is heated further until the starting material has disappeared (approximately 2 hours). The mixture is then cooled, added to ice-water and extracted with ethyl acetate. The extracts are washed with water, dried, evaporated and freed from traces of dimethylformamide under high vacuum at approximately 40° C. This gives 480 mg (yield virtually quantitative) of ethyl 6-cyano-2-trifluoromethylpyridin-3-ylcarboxylate in the form of an oil which slowly solidifies. 1H NMR (CDCl3, ppm): 8.29 (1H,d); 7.97 (1H,d); 4.48 (2H, d); 1.43 (3H,t).

Workup

  1. temperatureThe mixture is cooled overnight
  2. temperaturethe mixture is heated further until the starting material
  3. custom(approximately 2 hours)
  4. temperatureThe mixture is then cooled
  5. extractionextracted with ethyl acetate
  6. washThe extracts are washed with water
  7. customdried
  8. customevaporated
  9. customfreed from traces of dimethylformamide under high vacuum at approximately 40° C

Sources & evidence

ORD record
ord-2ff5c0b4cd32412f86933a958849dc27
Source dataset
uspto-grants-2002_12
Patent number
US06498125B2

Reaction notes

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