3-Aminopropionitrile → N-(2-cyanoethyl)-5-fluoro-4-fluoromethyl-4-(4-trifluoromethylphenoxy)-2-pentynamide

HRID 1282425Notes

Reaction equation

HRID 1282425 reaction equation
[F:1][CH2:2][C:3]([CH2:20][F:21])([O:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]([F:19])([F:18])[F:17])=[CH:12][CH:11]=1)[C:4]#[C:5][C:6](O)=[O:7].C(N(CC)CC)C.ClC(OCC)=O.[NH2:35][CH2:36][CH2:37][C:38]#[N:39]>ClCCl.CCCCCC.C(OCC)(=O)C>[C:36]([CH2:37][CH2:38][NH:39][C:6](=[O:7])[C:5]#[C:4][C:3]([CH2:2][F:1])([O:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]([F:19])([F:18])[F:17])=[CH:12][CH:11]=1)[CH2:20][F:21])#[N:35]

Participants

7

Reactant 4

HCID 16473-AminopropionitrileHCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 184243995-Fluoro-4-fluoromethyl-4-(4-trifluoromethylphenoxy)-2-pentynoic acid

Product 1

HCID 18424403N-(2-cyanoethyl)-5-fluoro-4-fluoromethyl-4-(4-trifluoromethylphenoxy)-2-pentynamideYield 93.3%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 21226206Ethyl acetate hexaneSolvent

Conditions

Temperature
-10 °C

Procedure

An amount (1.1 g) of 5-fluoro-4-fluoromethyl-4-(4-trifluoromethylphenoxy)-2-pentynoic acid and triethylamine (903 mg) were dissolved in dichloromethane (20 ml); to the solution under stirring at −10° C., ethyl chloroformate (464 mg) was added dropwise and the mixture was stirred at −10° C. for another one hour. Subsequently, 3-aminopropionitrile (500 mg) was added to the reaction mixture, followed by stirring at room temperature for 2 hours. To the reaction mixture, a hexane/ethyl acetate mixed solvent (1/1) was added and the resulting mixture was washed with 0.1 N HCl, a saturated aqueous solution of sodium hydrogencarbonate and a saturated aqueous solution of sodium chloride, dried with anhydrous sodium 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 (1.2 g) as a colorless oil.

Workup

  1. stirringthe mixture was stirred at −10° C. for another one hour
  2. stirringby stirring at room temperature for 2 hours
  3. washthe resulting mixture was washed with 0.1 N HCl
  4. dry with materiala saturated aqueous solution of sodium hydrogencarbonate and a saturated aqueous solution of sodium chloride, dried with anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-b8adab8d97a44a3a8af68363e2e16ab4
Source dataset
uspto-grants-2002_09
Patent number
US06455708B1

Reaction notes

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