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

HRID 1896054
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HRID 1896054 반응식
N[C:2]1([N+:21]([O-])=O)[C:7]([O:8][CH2:9][C:10]([F:13])([F:12])[F:11])=[CH:6][C:5]([CH3:14])=[N:4][CH:3]1[O:15][CH2:16][C:17]([F:20])([F:19])[F:18].CN(C)C1C=CC=CC=1.[Br:33][CH2:34][C:35](Br)=[O:36]>ClCCl>[Br:33][CH2:34][C:35]([NH:21][C:2]1[C:3]([O:15][CH2:16][C:17]([F:18])([F:19])[F:20])=[N:4][C:5]([CH3:14])=[CH:6][C:7]=1[O:8][CH2:9][C:10]([F:11])([F:12])[F:13])=[O:36]
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참가 물질

5

반응물 3

HCID 949N,N-DimethylanilineHCID 61147Bromoacetyl bromideHCID 230924323-Amino-2,4-bis(2,2,2-trifluoroethoxy)-6-methyl-3-nitropyridine

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

3-Amino-2,4-bis(2,2,2-trifluoroethoxy)-6-methyl-3-nitropyridine (42.29 g, 139.0 mmol) was dissolved in dichloromethane (600 mL), followed by the addition of N,N-dimethylaniline (20.46 g, 16.8 mmol). While stirring the mixture in an ice bath, a solution of bromoacetyl bromide (28.73 g, 142.3 mmol) in dichloromethane (100 mL) was added dropwise, and the reaction mixture was stirred at room temperature for 10 minutes. The reaction mixture was extracted with chloroform-water. The organic layer was washed with brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was recrystallized from chloroform-hexane to obtain the title compound (50.25 g, 85%) as colorless needles.

후처리

  1. stirringthe reaction mixture was stirred at room temperature for 10 minutes
  2. extractionThe reaction mixture was extracted with chloroform-water
  3. washThe organic layer was washed with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was recrystallized from chloroform-hexane

출처 및 근거

ORD 기록
ord-0ccebef96cd3486f837a1f6bcd1197d2
출처 데이터셋
uspto-grants-2013_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08518936B2

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