Malononitrile → 2-amino-1-(4-bromo-2,6-dimethylphenyl)-4-methyl-5-oxo-4,5-dihydro-1H-pyrrole-3-carbonitrile

HRID 1253828노트

반응식

HRID 1253828 반응식
[H-].[Na+].[C:3](#[N:7])[CH2:4][C:5]#[N:6].Br[CH:9]([CH3:22])[C:10]([NH:12][C:13]1[C:18]([CH3:19])=[CH:17][C:16]([Br:20])=[CH:15][C:14]=1[CH3:21])=[O:11].[Cl-].[NH4+]>O1CCCC1>[NH2:6][C:5]1[N:12]([C:13]2[C:18]([CH3:19])=[CH:17][C:16]([Br:20])=[CH:15][C:14]=2[CH3:21])[C:10](=[O:11])[CH:9]([CH3:22])[C:4]=1[C:3]#[N:7]

참가 물질

6

반응물 4

HCID 8010MalononitrileHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 600353552-bromo-N-(4-bromo-2,6-dimethylphenyl)propionamide

생성물 1

HCID 671036822-amino-1-(4-bromo-2,6-dimethylphenyl)-4-methyl-5-oxo-4,5-dihydro-1H-pyrrole-3-carbonitrile수율 96%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

To a suspension of NaH (17.2 g) in tetrahydrofuran (500 mL) was added a solution of malononitrile (28.4 g) in tetrahydrofuran (100 mL) under ice-cooling and the mixture was stirred at room temperature for 1 hour. 2-Bromo-N-(4-bromo-2,6-dimethylphenyl)propionamide (120 g) was added and the mixture was heated at reflux for 1 hour. With ice-cooling, an ammonium chloride aqueous solution was added and extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated under reduced pressure to give a solid. The solid was washed with a mixture of diisopropylether and ethyl acetate and filtered, dried to give 2-amino-1-(4-bromo-2,6-dimethylphenyl)-4-methyl-5-oxo-4,5-dihydro-1H-pyrrole-3-carbonitrile (110.1 g).

후처리

  1. temperaturecooling
  2. temperaturethe mixture was heated
  3. temperatureat reflux for 1 hour
  4. temperatureWith ice-cooling
  5. extractionextracted with ethyl acetate
  6. washThe organic layer was washed with brine
  7. dry with materialdried over anhydrous sodium sulfate
  8. filtrationfiltered
  9. concentrationThe filtrate was concentrated under reduced pressure
  10. customto give a solid
  11. washThe solid was washed with a mixture of diisopropylether and ethyl acetate
  12. filtrationfiltered
  13. customdried

출처 및 근거

ORD 기록
ord-d7ccaa947a30472094bbdd663e11d824
출처 데이터셋
uspto-grants-2013_06
특허 번호
US08455511B2

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