Ammonium Chloride → N-(2-cyanoethyl)-5-fluoro-4-fluoromethyl-4-(4-trifluoromethylphenoxy)-2-pentynamide

HRID 1282426Notes

Reaction equation

HRID 1282426 reaction equation
[F:1][C:2]([F:18])([F:17])[C:3]1[CH:8]=[CH:7][C:6]([O:9][C:10]([CH2:15][F:16])([C:13]#[CH:14])[CH2:11][F:12])=[CH:5][CH:4]=1.C([Li])CCC.[C:24]([CH2:26][CH2:27][N:28]=[C:29]=[O:30])#[N:25].[Cl-].[NH4+]>COC(C)(C)C>[C:24]([CH2:26][CH2:27][NH:28][C:29](=[O:30])[C:14]#[C:13][C:10]([CH2:11][F:12])([O:9][C:6]1[CH:7]=[CH:8][C:3]([C:2]([F:17])([F:18])[F:1])=[CH:4][CH:5]=1)[CH2:15][F:16])#[N:25]

Participants

6

Reactant 4

HCID 25517Ammonium ChlorideHCID 184244041-Fluoro-2-fluoromethyl-3-butyn-2-yl 4-trifluoromethylphenyl etherHCID 184244233-IsocyanatopropanenitrileHCID 178418339Butyllithium

Product 1

HCID 18424403N-(2-cyanoethyl)-5-fluoro-4-fluoromethyl-4-(4-trifluoromethylphenoxy)-2-pentynamideYield 54.1%

Reagents, catalysts & solvents 1

HCID 15413tert-Butyl methyl etherSolvent

Procedure

An amount (61 mg) of 1-fluoro-2-fluoromethyl-3-butyn-2-yl 4-trifluoromethylphenyl ether was dissolved in t-butyl methyl ether (2 ml); to the solution, 1.69 M n-butyllithium (0.148 ml) was added at −70° C. under a nitrogen atmosphere and the mixture was stirred for 10 minutes. To the reaction mixture, 2-cyanoethyl isocyanate (28 mg) was added and the resulting mixture was stirred at −70° C. for 10 minutes. To the reaction mixture, a saturated aqueous solution of ammonium chloride was added, followed by extraction with hexane/ethyl acetate (1/1); the resulting organic layers were washed with a 1 N aqueous solution of sodium hydroxide and a saturated aqueous solution of sodium chloride, dried with anhydrous sulfate and concentrated under reduced pressure; the resulting residue was subjected to silica gel column chromatography (eluent; hexane/ethyl acetate=3/2) to give the titled compound (45 mg) as a colorless oil.

Workup

  1. stirringthe resulting mixture was stirred at −70° C. for 10 minutes
  2. extractionfollowed by extraction with hexane/ethyl acetate (1/1)
  3. washthe resulting organic layers were washed with a 1 N aqueous solution of sodium hydroxide
  4. dry with materiala saturated aqueous solution of sodium chloride, dried with anhydrous sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-f9c490138d8d40aca3e89740dcc3aa18
Source dataset
uspto-grants-2002_09
Patent number
US06455708B1

Reaction notes

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