Water → 5-Fluoro-2-{2-(methoxycarbonyl)methoxyphenoxy}-4-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-1,2,3,6-tetrahydropyrimidin-1-yl]aniline

HRID 433736ノート

反応式

HRID 433736 の反応式
O.[F:2][C:3]1[C:4]([N:25]2[C:30](=[O:31])[CH:29]=[C:28]([C:32]([F:35])([F:34])[F:33])[N:27]([CH3:36])[C:26]2=[O:37])=[CH:5][C:6]([O:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[O:19][CH2:20][C:21]([O:23][CH3:24])=[O:22])=[C:7]([N+:9]([O-])=O)[CH:8]=1>C(O)(=O)C.[Fe]>[F:2][C:3]1[C:4]([N:25]2[C:30](=[O:31])[CH:29]=[C:28]([C:32]([F:33])([F:34])[F:35])[N:27]([CH3:36])[C:26]2=[O:37])=[CH:5][C:6]([O:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[O:19][CH2:20][C:21]([O:23][CH3:24])=[O:22])=[C:7]([CH:8]=1)[NH2:9]

参加物

5

反応物 2

HCID 962WaterHCID 187592902-{2-(Methoxycarbonyl)methoxyphenoxy}-5-fluoro-4-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-1,2,3,6-tetrahydropyrimidin-1-yl]nitrobenzene

生成物 1

HCID 187593175-Fluoro-2-{2-(methoxycarbonyl)methoxyphenoxy}-4-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-1,2,3,6-tetrahydropyrimidin-1-yl]aniline収率 84.2%

試薬・触媒・溶媒 2

HCID 23925Iron触媒HCID 176Acetic Acid溶媒2 回

実験手順

To a solution of 19 g of iron powder, 60 ml of acetic acid and 6 ml of water, a solution of 19.12 g of 5-fluoro-2-{2-(methoxycarbonyl)methoxyphenoxy}-4-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-1,2,3,6-tetrahydropyrimidin-1-yl]nitrobenzene [Compound 4-19 of the present invention] in 60 ml of acetic acid was added dropwise under ice cooling. After the addition, the temperature of the reaction mixture was raised to room temperature and the mixture was stirred for 4 hours. The reaction mixture was filtered with sellaite and diluted with ethyl acetate. The dilution was washed with water, saturated aqueous sodium bicarbonate solution and saturated saline, dried over anhydrous magnesium sulfate, and concentrated. The residue was subjected to silica gel column chromatography to obtain 15.16 g of 5-fluoro-2-{2-(methoxycarbonyl)methoxyphenoxy}-4-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-1,2,3,6-tetrahydropyrimidin-1-yl]aniline.

後処理

  1. additionAfter the addition
  2. filtrationThe reaction mixture was filtered with sellaite
  3. additiondiluted with ethyl acetate
  4. washThe dilution was washed with water, saturated aqueous sodium bicarbonate solution and saturated saline
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated

出典と根拠

ORDレコード
ord-6eaee47defd64eabb29876da3e5c61af
出典データセット
uspto-grants-2003_12
特許番号
US06667413B2

反応ノート

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