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Dimethylformamide → N-phenyl-4-methoxy-6-{3-(trifluoromethoxy)phenoxy}-2-pyridine carboxamide

HRID 1250480
ノート
印刷プレビュー

反応式

HRID 1250480 の反応式
[F:1][C:2]([F:12])([F:11])[O:3][C:4]1[CH:5]=[C:6]([OH:10])[CH:7]=[CH:8][CH:9]=1.[H-].[Na+].Br[C:16]1[CH:21]=[C:20]([O:22][CH3:23])[CH:19]=[C:18](Br)[N:17]=1.[CH3:25][N:26]([CH:28]=[O:29])C>CCCCCC>[C:25]1([NH:26][C:28]([C:16]2[CH:21]=[C:20]([O:22][CH3:23])[CH:19]=[C:18]([O:10][C:6]3[CH:7]=[CH:8][CH:9]=[C:4]([O:3][C:2]([F:11])([F:12])[F:1])[CH:5]=3)[N:17]=2)=[O:29])[CH:6]=[CH:5][CH:4]=[CH:9][CH:8]=1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 27332613-(Trifluoromethoxy)phenolHCID 109015692,6-Dibromo-4-methoxypyridine

生成物 1

HCID 15906599N-phenyl-4-methoxy-6-{3-(trifluoromethoxy)phenoxy}-2-pyridine carboxamide

試薬・触媒・溶媒 1

HCID 8058Hexane
溶媒

反応条件

温度
110 °C

実験手順

2.00 g (0.00937×1.2 mol) of 3-(trifluoromethoxy) phenol was dissolved in about 20 ml of DMF. The solution was further mixed with 0.39 g (ca. 60% in mineral oil; 0.00937×1.04 mol) of NaH and then with 2.50 g (0.00937 mol) of 2,6-dibromo-4-methoxy pyridine. After stirring at about 110° C. for about 4 hours, the obtained mixture was allowed to stand for cooling to room temperature. After the reaction solution was distributed in hexane-saturated sodium bicarbonate water, the organic phase of the obtained solution was washed with saturated brine and dried with anhydrous sodium sulfate. The resultant solution was concentrated and then purified by silica gel column chromatography (eluting solution: ethyl acetate/hexane), and the obtained eluate was subjected to recrystallization using hexane, thereby obtaining an aimed product.

後処理

  1. temperaturefor cooling to room temperature
  2. washthe organic phase of the obtained solution was washed with saturated brine
  3. dry with materialdried with anhydrous sodium sulfate
  4. concentrationThe resultant solution was concentrated
  5. custompurified by silica gel column chromatography (eluting solution: ethyl acetate/hexane)
  6. customthe obtained eluate was subjected to recrystallization

出典と根拠

ORDレコード
ord-f679f1a0be3743e791a0679138d9e2cb
出典データセット
uspto-grants-2002_01
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06339045B1

反応ノート

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