3-(Trifluoromethyl)phenol → HCID 2821109, compound

HRID 1585469Notes

Reaction equation

HRID 1585469 reaction equation
[F:1][C:2]([F:11])([F:10])[C:3]1[CH:4]=[C:5]([OH:9])[CH:6]=[CH:7][CH:8]=1.[H-].[Na+].Cl[C:15]1[C:20]([C:21]#[N:22])=[N:19][CH:18]=[CH:17][N:16]=1>O1CCCC1>[F:1][C:2]([F:10])([F:11])[C:3]1[CH:4]=[C:5]([CH:6]=[CH:7][CH:8]=1)[O:9][C:15]1[C:20]([C:21]#[N:22])=[N:19][CH:18]=[CH:17][N:16]=1

Participants

5

Reactant 3

HCID 73763-(Trifluoromethyl)phenolHCID 24758Sodium hydrideHCID 2924653-Chloropyrazine-2-carbonitrile

Product 1

HCID 2821109HCID 2821109, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

12.8 g (80 mmol) of 3-trifluoromethylphenol are added to a suspension of 2.2 g (90 mmol) of sodium hydride in 40 ml of tetrahydrofuran. The reaction mixture is heated to the boil. After 1 hour, a solution of 11.2 g (80 mmol) of 2-chloro-3-cyanopyrazine in 40 ml of tetrahydrofuran is added and the mixture is heated at the boil for a further 4 hours. After the mixture has cooled to room temperature, the solvent is distilled off under reduced pressure. The residue is taken up in diethyl ether and the solution is extracted with 5% strength, aqueous sodium hydroxide solution, washed with distilled water, dried over magnesium sulfate, filtered and freed from the solvent under reduced pressure. The crude product is purified by chromatography (silica gel, cyclohexane/ethyl acetate 20/1 (v/v)). 4.6 g (51%) of a yellow, crystalline solid of melting point 68-70° C. are obtained.

Workup

  1. temperatureThe reaction mixture is heated to the boil
  2. temperaturethe mixture is heated at the boil for a further 4 hours
  3. distillationthe solvent is distilled off under reduced pressure
  4. extractionthe solution is extracted with 5% strength, aqueous sodium hydroxide solution
  5. washwashed with distilled water
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. customThe crude product is purified by chromatography (silica gel, cyclohexane/ethyl acetate 20/1 (v/v))
  9. custom4.6 g (51%) of a yellow, crystalline solid of melting point 68-70° C. are obtained

Sources & evidence

ORD record
ord-4adde5110bf445b0b5dd155d23e14b55
Source dataset
uspto-grants-1999_08
Patent number
US05939359

Reaction notes

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