Phenylacetonitrile → 3-(Dimethylamino)-2-phenylacrylonitrile

HRID 1779392노트

반응식

HRID 1779392 반응식
[CH2:1]([C:8]#[N:9])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CO[CH:12](OC)[N:13]([CH3:15])[CH3:14]>CO>[C:8]([C:1]([C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)=[CH:12][N:13]([CH3:15])[CH3:14])#[N:9]

참가 물질

4

반응물 2

HCID 8794PhenylacetonitrileHCID 78373Dimethylformamide dimethyl acetal

생성물 1

HCID 37978433-(Dimethylamino)-2-phenylacrylonitrile수율 77.9%

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

A stirred solution of 5.1 grams (0.044 mole) of benzyl cyanide and 8.7 grams (0.065 mole) of N,N-dimethylformamide dimethyl acetal in 150 mL of methanol was heated at reflux for about 20 hours. After this time gas chromatographic analysis of the reaction mixture indicated that the reaction was not complete. An additional 3.0 mL of the intermediate acetal (total--0.088 mole) was added, and the heating at reflux was continued an additional 24 hours. After this time the reaction mixture was concentrated under reduced pressure to a residue. The residue was triturated with 25% methylene chloride in petroleum ether, yielding 5.9 grams of 1-cyano-1-phenyl-2-(N,N-dimethylamino)ethene. The NMR spectrum was consistent with the proposed structure.

후처리

  1. temperatureat reflux for about 20 hours
  2. temperaturethe heating at reflux
  3. concentrationAfter this time the reaction mixture was concentrated under reduced pressure to a residue
  4. customThe residue was triturated with 25% methylene chloride in petroleum ether

출처 및 근거

ORD 기록
ord-55118f01321b463e81cf398454f5672b
출처 데이터셋
uspto-grants-1997_05
특허 번호
US05627189

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