Dimethylformamide → 2-[[3-[(5-Methyl-2-phenyl-4-thiazolyl)methoxy]-5-isoxazolyl]methoxy]nicotinonitrile

HRID 1294193ノート

反応式

HRID 1294193 の反応式
[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:15]1[CH:19]=[C:18]([CH2:20][OH:21])[O:17][N:16]=1.Cl[C:23]1[C:28]([C:29]#[N:30])=[CH:27][CH:26]=[CH:25][N:24]=1.CN(C)C=O.[H-].[Na+]>O>[CH3:1][C:2]1[S:6][C:5]([C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=2)=[N:4][C:3]=1[CH2:13][O:14][C:15]1[CH:19]=[C:18]([CH2:20][O:21][C:23]2[N:24]=[CH:25][CH:26]=[CH:27][C:28]=2[C:29]#[N:30])[O:17][N:16]=1

参加物

6

反応物 4

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 810792-ChloronicotinonitrileHCID 178613523-(5-Methyl-2-phenyl-4-thiazolylmethoxy)-5-isoxazolylmethanol

生成物 1

HCID 688859742-[[3-[(5-Methyl-2-phenyl-4-thiazolyl)methoxy]-5-isoxazolyl]methoxy]nicotinonitrile収率 86.4%

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

To a mixture of [3-(5-methyl-2-phenyl-4-thiazolylmethoxy)-5-isoxazolyl]methanol (1.80 g), 2-chloro-3-cyanopyridine (0.83 g) and N,N-dimethylformamide (80 mL) was added sodium hydride (60%, oil, 0.26 g) under ice-cooling. The reaction mixture was stirred at room temperature for 5 hrs. 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 (2.08 g, 86%) of 2-[[3-[(5-methyl-2-phenyl-4-thiazolyl)methoxy]-5-isoxazolyl]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: 135-136° C.

後処理

  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

出典と根拠

ORDレコード
ord-455c960a77d24187a5937225799744f8
出典データセット
uspto-grants-2007_07
特許番号
US07238716B2

反応ノート

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