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N,N-Dimethylaniline → 2-bromo-N-[2,4-bis(2,2,2-trifluoroethoxy)-6-methylpyridin-3-yl]acetamide

HRID 1354256
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HRID 1354256 반응식
CN(C)C1C=CC=CC=1.[NH2:10][C:11]1[C:12]([O:24][CH2:25][C:26]([F:29])([F:28])[F:27])=[N:13][C:14]([CH3:23])=[CH:15][C:16]=1[O:17][CH2:18][C:19]([F:22])([F:21])[F:20].[Br:30][CH2:31][C:32](Br)=[O:33]>ClCCl.O>[Br:30][CH2:31][C:32]([NH:10][C:11]1[C:12]([O:24][CH2:25][C:26]([F:29])([F:27])[F:28])=[N:13][C:14]([CH3:23])=[CH:15][C:16]=1[O:17][CH2:18][C:19]([F:21])([F:22])[F:20])=[O:33]
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참가 물질

6

반응물 3

HCID 949N,N-DimethylanilineHCID 61147Bromoacetyl bromideHCID 230924336-Methyl-2,4-bis(2,2,2-trifluoroethoxy)pyridin-3-amine

생성물 1

HCID 115899302-bromo-N-[2,4-bis(2,2,2-trifluoroethoxy)-6-methylpyridin-3-yl]acetamide수율 85%

시약·촉매·용매 2

HCID 962Water용매
HCID 6344
Dichloromethane
용매
2회

실험 절차

N,N-Dimethylaniline (20.46 g, 168.8 mmol) was added to a solution of 3-amino-2,4-bis(2,2,2-trifluoroethoxy)-6-methylpyridine (42.29 g, 139.0 mmol) in dichloromethane (600 mL). While the mixture was stirred under cooling with ice, a solution of bromoacetyl bromide (28.73 g, 142.3 mmol) in dichloromethane (100 mL) was added thereto, followed by stirring for ten minutes. The reaction mixture was diluted with water and then extracted with chloroform. The organic layer was washed with saturated brine and then dried over sodium sulfate anhydrate, followed by concentration under reduced pressure. The thus-obtained crystals were recrystallized from chloroform-hexane, to thereby yield 2-bromo-N-[2,4-bis(2,2,2-trifluoroethoxy)-6-methylpyridin-3-yl]acetamide (50.25 g, yield 85%) as colorless needles.

후처리

  1. temperatureunder cooling with ice
  2. stirringby stirring for ten minutes
  3. extractionextracted with chloroform
  4. washThe organic layer was washed with saturated brine
  5. dry with materialdried over sodium sulfate anhydrate
  6. concentrationfollowed by concentration under reduced pressure
  7. customThe thus-obtained crystals were recrystallized from chloroform-hexane

출처 및 근거

ORD 기록
ord-f52ff6db4e1e4bddbb770aab5a651433
출처 데이터셋
uspto-grants-2007_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07223764B2

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