Dimethylformamide → 6-[(5-Methyl-2-phenyl-4-thiazolyl)methoxy]nicotinonitrile

HRID 1294200노트

반응식

HRID 1294200 반응식
[CH3:1][C:2]1[S:6][C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[N:4][C:3]=1[CH2:13][OH:14].Cl[C:16]1[N:21]=[CH:20][C:19]([C:22]#[N:23])=[CH:18][CH:17]=1.CN(C)C=O.[H-].[Na+]>O>[CH3:1][C:2]1[S:6][C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[N:4][C:3]=1[CH2:13][O:14][C:16]1[CH:17]=[CH:18][C:19]([C:22]#[N:23])=[CH:20][N:21]=1

참가 물질

6

반응물 4

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 51520946-Chloro-3-pyridinecarbonitrileHCID 22494033(5-Methyl-2-phenyl-4-thiazolyl)methanol

생성물 1

HCID 688845976-[(5-Methyl-2-phenyl-4-thiazolyl)methoxy]nicotinonitrile수율 74.1%

시약·촉매·용매 1

HCID 962Water용매

실험 절차

To a mixture of (5-methyl-2-phenyl-4-thiazolyl)methanol (5.0 g), 6-chloro-3-cyanopyridine (3.38 g) and N,N-dimethylformamide (100 mL) was added sodium hydride (60%, oil, 1.07 g) under ice-cooling. The reaction mixture was stirred at room temperature for 1 hr. Water was added to the reaction mixture and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated. The obtained residue was subjected to silica gel column chromatography to give crystals (5.55 g, 74%) of 6-[(5-methyl-2-phenyl-4-thiazolyl)methoxy]nicotinonitrile from a fraction eluted with ethyl acetate-hexane (1:2, v/v). Recrystallization from ethyl acetate-hexane gave colorless prism crystals. melting point: 124-125° C.

후처리

  1. temperaturecooling
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated

출처 및 근거

ORD 기록
ord-9869aef00e7048f8a241a9211482b123
출처 데이터셋
uspto-grants-2007_07
특허 번호
US07238716B2

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