Acetonitrile → HCID 23614502, compound

HRID 1767928Notes

Reaction equation

HRID 1767928 reaction equation
Cl[CH2:2][C:3]1[S:7][C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([C:14]([F:17])([F:16])[F:15])[CH:9]=2)=[N:5][C:4]=1[CH3:18].C(=O)(O)[O-].[Na+].C(OCC)(=O)C.[C:30](#[N:32])C>[C-]#N.C([N+](CCCC)(CCCC)CCCC)CCC>[CH3:18][C:4]1[N:5]=[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([C:14]([F:17])([F:16])[F:15])[CH:9]=2)[S:7][C:3]=1[CH2:2][C:30]#[N:32]

Participants

6

Reactant 4

HCID 6342AcetonitrileHCID 8857Ethyl AcetateHCID 516892Sodium BicarbonateHCID 236145055-(Chloromethyl)-4-methyl-2-[3-(trifluoromethyl)phenyl]-1,3-thiazole

Product 1

HCID 23614502HCID 23614502, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 165872Tetrabutylammonium CyanideCatalyst

Procedure

Tetrabutylammonium cyanide (1.44 g, 5.4 mmol) was added to a solution of 5-chloromethyl-4-methyl-2-(3-trifluoromethyl-phenyl)-thiazole (1.2 g, 4.1 mmol) in acetonitrile (27 ml). The solution was stirred at ambient temperature for 16 h, saturated aqueous sodium bicarbonate solution/ice water 1/1 and ethyl acetate were added and the layers were separated. The aqueous layer was extracted with ethyl acetate, the combined organic layers were washed with ice water/brine 1/1, dried over sodium sulfate and the solvent was evaporated in vacuo to give brown oil which was purified by column chromatography (silica gel, pentane/ethyl acetate) to yield 700 mg (2.5 mmol, 60%) of the title compound as orange oil.

Workup

  1. customthe layers were separated
  2. extractionThe aqueous layer was extracted with ethyl acetate
  3. washthe combined organic layers were washed with ice water/brine 1/1
  4. dry with materialdried over sodium sulfate
  5. customthe solvent was evaporated in vacuo
  6. customto give brown oil which
  7. customwas purified by column chromatography (silica gel, pentane/ethyl acetate)

Sources & evidence

ORD record
ord-4b13b2bf8e724a7d800bce8625e48a91
Source dataset
uspto-grants-2007_06
Patent number
US07235572B2

Reaction notes

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