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Methanol → 5,5-Dimethyl-1-(6-hydroxyquinoline-4-ylmethyl)-3-(4-trifluoromethoxyphenyl)imidazolidine-2,4-dione

HRID 899968
ノート
印刷プレビュー

反応式

HRID 899968 の反応式
B(Br)(Br)Br.[CH3:5][C:6]1([CH3:37])[N:10]([CH2:11][C:12]2[C:21]3[C:16](=[CH:17][CH:18]=[C:19]([O:22]C)[CH:20]=3)[N:15]=[CH:14][CH:13]=2)[C:9](=[O:24])[N:8]([C:25]2[CH:30]=[CH:29][C:28]([O:31][C:32]([F:35])([F:34])[F:33])=[CH:27][CH:26]=2)[C:7]1=[O:36].CO.C([O-])(O)=O.[Na+]>C(Cl)Cl.O>[CH3:5][C:6]1([CH3:37])[N:10]([CH2:11][C:12]2[C:21]3[C:16](=[CH:17][CH:18]=[C:19]([OH:22])[CH:20]=3)[N:15]=[CH:14][CH:13]=2)[C:9](=[O:24])[N:8]([C:25]2[CH:26]=[CH:27][C:28]([O:31][C:32]([F:34])([F:35])[F:33])=[CH:29][CH:30]=2)[C:7]1=[O:36]
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

7

反応物 4

HCID 887MethanolHCID 25134Boron tribromideHCID 516892Sodium BicarbonateHCID 596942685,5-Dimethyl-1-(6-methoxyquinolin-4-ylmethyl)-3-(4-trifluoromethoxyphenyl)imidazolidine-2,4-dione

生成物 1

HCID 596942575,5-Dimethyl-1-(6-hydroxyquinoline-4-ylmethyl)-3-(4-trifluoromethoxyphenyl)imidazolidine-2,4-dione収率 67.4%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6344Dichloromethane溶媒3 回

反応条件

温度
20 °C

実験手順

6 ml of a 1M solution of boron tribromide in CH2Cl2 are added to a solution of 0.26 g of 5,5-dimethyl-1-(6-methoxyquinolin-4-ylmethyl)-3-(4-trifluoromethoxyphenyl)imidazolidine-2,4-dione in 40 ml of dichloromethane, under an inert atmosphere of argon at a temperature in the region of 0° C. The reaction medium is stirred at a temperature in the region of 20° C. for 16 hours. 5 ml of methanol are added dropwise. After stirring for 30 minutes at this temperature, 50 ml of water, 30 ml of CH2Cl2 and 10 ml of saturated NaHCO3 are added. After separation of the phases by settling, the organic phase is dried over sodium sulfate, filtered and then concentrated under reduced pressure. The beige-colored foam obtained is purified by flash chromatography (SiO2, EtOAc as eluent, Ar). The fractions containing the product are concentrated under reduced pressure. 0.17 g of 5,5-dimethyl-1-(6-hydroxyquinoline-4-ylmethyl)-3-(4-trifluoromethoxyphenyl)imidazolidine-2,4-dione is thus obtained, the characteristics of which product are as follows:

後処理

  1. additionare added
  2. customAfter separation of the phases
  3. dry with materialthe organic phase is dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe beige-colored foam obtained
  7. customis purified by flash chromatography (SiO2, EtOAc as eluent, Ar)
  8. additionThe fractions containing the product
  9. concentrationare concentrated under reduced pressure

出典と根拠

ORDレコード
ord-66d819150265469bb71e9a2a7d649ebc
出典データセット
uspto-grants-2008_04
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07354933B2

反応ノート

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