Sodium Iodide → 2-[2-Chloro-4-fluoro-5-(3-methyl-2,6-dioxo-4-trifluoromethyl-1,2,3,6-tetrahydropyrimidin-1-yl)phenoxy]-2-(methylthio)acetamide

HRID 1354561ノート

反応式

HRID 1354561 の反応式
[H-].[Na+].[Cl:3][C:4]1[CH:9]=[C:8]([F:10])[C:7]([N:11]2[C:16](=[O:17])[CH:15]=[C:14]([C:18]([F:21])([F:20])[F:19])[N:13]([CH3:22])[C:12]2=[O:23])=[CH:6][C:5]=1[OH:24].[I-].[Na+].Cl[CH:28]([S:32][CH3:33])[C:29]([NH2:31])=[O:30]>O.C(COC)OC>[Cl:3][C:4]1[CH:9]=[C:8]([F:10])[C:7]([N:11]2[C:16](=[O:17])[CH:15]=[C:14]([C:18]([F:20])([F:21])[F:19])[N:13]([CH3:22])[C:12]2=[O:23])=[CH:6][C:5]=1[O:24][CH:28]([S:32][CH3:33])[C:29]([NH2:31])=[O:30]

参加物

7

反応物 4

HCID 5238Sodium IodideHCID 24758Sodium hydrideHCID 112677571-methyl-6-trifluoromethyl-3-(4-chloro-2-fluoro-5-hydroxyphenyl)-2,4(1H,3H)-pyrimidinedioneHCID 229383202-Chloro-2-(methylthio)acetamide

生成物 1

HCID 210719342-[2-Chloro-4-fluoro-5-(3-methyl-2,6-dioxo-4-trifluoromethyl-1,2,3,6-tetrahydropyrimidin-1-yl)phenoxy]-2-(methylthio)acetamide収率 78.2%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 80711,2-Dimethoxyethane溶媒

実験手順

To a mixture of 1.3 g of sodium hydride and 100 ml of dimethoxyethane, 10 g of 2-chloro-4-fluoro-5-(3-methyl-2,6-dioxo-4-trifluoromethyl-1,2,3,6-tetrahydropyrimidin-1-yl)phenol were added at room temperature and stirred for 30 minutes. Then, 2.2 g of sodium iodide and 6.7 g of crude 2-chloro-2-(methylthio)acetamide were added thereto and stirred at room temperature for 3 hours, and water was poured into the reaction mixture. The reaction mixture was extracted with ethyl acetate. The organic layer was washed with aqueous sodium bicarbonate solution, dried over anhydrous magnesium sulfate and concentrated. The residue was subjected to silica gel column chromatography (eluent: ethyl acetate) to give 10.2 g of 2-[2-chloro-4-fluoro-5-(3-methyl-2,6-dioxo-4-trifluoromethyl-1,2,3,6-tetrahydropyrimidin-1-yl)phenoxy]-2-(methylthio) acetamide.

後処理

  1. additionwere added at room temperature
  2. stirringstirred at room temperature for 3 hours
  3. extractionThe reaction mixture was extracted with ethyl acetate
  4. washThe organic layer was washed with aqueous sodium bicarbonate solution
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated

出典と根拠

ORDレコード
ord-dcdda0c73d6a4e329aa662799e8a99e9
出典データセット
uspto-grants-2007_05
特許番号
US07223862B2

反応ノート

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