Hydrochloric Acid → 3-[(4,4,4-Trifluoro-3-oxo-1-butenyl)amino]-2-propenenitrile

HRID 1744268노트

반응식

HRID 1744268 반응식
[H-].[Na+].[NH2:3][CH:4]=[CH:5][C:6](=[O:11])[C:7]([F:10])([F:9])[F:8].CO[CH:14](OC)[CH2:15][C:16]#[N:17].Cl>CN(C)C=O.CCCCCC.C(OCC)(=O)C.O>[F:8][C:7]([F:10])([F:9])[C:6](=[O:11])[CH:5]=[CH:4][NH:3][CH:14]=[CH:15][C:16]#[N:17]

참가 물질

8

반응물 4

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 937313,3-DimethoxypropiononitrileHCID 27794423-Buten-2-one, 4-amino-1,1,1-trifluoro-, (3Z)-

생성물 1

HCID 731022503-[(4,4,4-Trifluoro-3-oxo-1-butenyl)amino]-2-propenenitrile수율 13.2%

시약·촉매·용매 3

HCID 962Water용매HCID 6228Dimethylformamide용매HCID 21226206Ethyl acetate hexane용매

실험 절차

Sodium hydride (60% dispersion in mineral oil, 400 mg, 10 mmol) was charged and washed with hexane twice. Into this flask, N,N-dimethylformamide (15 ml) was added and a solution prepared by dissolving 4-amino-1,1,1-trifluoro-3-buten-2-one (1.4 g, 10 mmol) and. 3,3-dimethoxypropionitrile (1.15 g, 10 mmol) in N,N-dimethylformamide (5 ml) was added dropwise under ice-cooling. After stirring the mixture at room temperature for 4 hours, the reaction mixture was poured into water (50 ml). This mixture was acidified with concentrated hydrochloric acid and then extracted with ethyl acetate. The organic layers were combined, washed with brine, dried over magnesium sulfate and then concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (a eluting solvent: hexane/ethyl acetate=3/1 to 1/1) to obtain 251 mg (yield 13.2%) of title compound (IIa) having a low polarity and 372 mg (yield 19.8%) of title compound (IIb) having a high polarity.

후처리

  1. washwashed with hexane twice
  2. additionInto this flask, N,N-dimethylformamide (15 ml) was added
  3. customa solution prepared
  4. temperaturecooling
  5. extractionextracted with ethyl acetate
  6. washwashed with brine
  7. dry with materialdried over magnesium sulfate
  8. concentrationconcentrated under reduced pressure
  9. customThe resulting residue was purified by silica gel column chromatography (a eluting solvent

출처 및 근거

ORD 기록
ord-071837d2e9324e2cae40641ebf91bf67
출처 데이터셋
uspto-grants-2006_03
특허 번호
US07015236B2

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