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

HRID 1282425
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HRID 1282425 반응식
[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]
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참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 6344
Dichloromethane
용매
HCID 21226206Ethyl acetate hexane용매

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온도
-10 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-b8adab8d97a44a3a8af68363e2e16ab4
출처 데이터셋
uspto-grants-2002_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06455708B1

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