Sodium hydride → 3-(1-Methyl-5-triphenylmethylaminopyrazol-4-yl)acrylonitrile

HRID 349538노트

반응식

HRID 349538 반응식
[H-].[Na+].C(OP([CH2:11][C:12]#[N:13])(=O)OCC)C.[CH3:14][N:15]1[C:19]([NH:20][C:21]([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[C:18]([CH:40]=O)[CH:17]=[N:16]1>O1CCCC1>[CH3:14][N:15]1[C:19]([NH:20][C:21]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)([C:34]2[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=2)[C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[C:18]([CH:40]=[CH:11][C:12]#[N:13])[CH:17]=[N:16]1

참가 물질

5

반응물 3

HCID 24758Sodium hydrideHCID 75676Diethyl (cyanomethyl)phosphonateHCID 179619601-Methyl-5-triphenylmethylaminopyrazole-4-carbaldehyde

생성물 1

HCID 693317453-(1-Methyl-5-triphenylmethylaminopyrazol-4-yl)acrylonitrile수율 60.9%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a suspension of sodium hydride (55% dispersion in mineral oil, 26.2 g, 600 mmol) in tetrahydrofuran (1000 ml) was added diethyl(cyanomethyl)phosphonate (106.3 g, 600 mmol) under ice-cooling. The mixture was stirred under ice-cooling for 20 minutes. To the mixture was added 1-methyl-5-triphenylmethylaminopyrazole-4-carbaldehyde (197 g, 530 mmol), and the mixture was stirred for 2 hours. The reaction mixture was poured into ice-cold water. The mixture was extracted with ethyl acetate. The extract was dried over anhydrous magnesium sulfate, filtered, and concentrated in vacuo. The residue was triturated with diethyl ether to give 3-(1-methyl-5-triphenylmethylaminopyrazol-4-yl)acrylonitrile (E, Z mixture, 126 g) as a solid.

후처리

  1. temperaturecooling
  2. temperaturecooling for 20 minutes
  3. stirringthe mixture was stirred for 2 hours
  4. additionThe reaction mixture was poured into ice-cold water
  5. extractionThe mixture was extracted with ethyl acetate
  6. dry with materialThe extract was dried over anhydrous magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe residue was triturated with diethyl ether

출처 및 근거

ORD 기록
ord-efdb7497533745a4a77875ee3583e194
출처 데이터셋
uspto-grants-2007_02
특허 번호
US07179801B2

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