Tetrahydrofuran → Allyl [2-{2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-1,2,3,6-tetrahydropyrimidin-1-yl]phenoxy}phenoxy]acetate

HRID 493925ノート

反応式

HRID 493925 の反応式
[Cl:1][C:2]1[CH:19]=[C:18]([F:20])[C:17]([N:21]2[C:26](=[O:27])[CH:25]=[C:24]([C:28]([F:31])([F:30])[F:29])[N:23]([CH3:32])[C:22]2=[O:33])=[CH:16][C:3]=1[O:4][C:5]1[CH:15]=[CH:14][CH:13]=[CH:12][C:6]=1[O:7][CH2:8][C:9]([OH:11])=[O:10].O1C[CH2:37][CH2:36][CH2:35]1>S(Cl)(Cl)=O>[Cl:1][C:2]1[CH:19]=[C:18]([F:20])[C:17]([N:21]2[C:26](=[O:27])[CH:25]=[C:24]([C:28]([F:29])([F:30])[F:31])[N:23]([CH3:32])[C:22]2=[O:33])=[CH:16][C:3]=1[O:4][C:5]1[CH:15]=[CH:14][CH:13]=[CH:12][C:6]=1[O:7][CH2:8][C:9]([O:11][CH2:37][CH:36]=[CH2:35])=[O:10]

参加物

4

反応物 2

HCID 8028TetrahydrofuranHCID 21933550[2-{2-Chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-1,2,3,6-tetrahydropyrimidin-1-yl]phenoxy}phenoxy]acetic acid

生成物 1

HCID 17812332Allyl [2-{2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-1,2,3,6-tetrahydropyrimidin-1-yl]phenoxy}phenoxy]acetate

試薬・触媒・溶媒 1

HCID 24386Thionyl Chloride溶媒

実験手順

First, 1.0 g of [2-{2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-1,2,3,6-tetrahydropyrimidin-1-yl]phenoxy}phenoxy]acetic acid (compound a-1) was dissolved in tetrahydrofuran, to which 0.7 ml of thionyl chloride was added under stirring, and the mixture was heated and stirred under reflux for 2 hours. After left for cooling and the subsequent concentration, the residue was dissolved in 3 ml of tetrahydrofuran (hereinafter referred to as solution B). Then, 0.7 ml of tetrahydrofuran was added to 0.05 g of allyl alcohol, to which a third part of solution B was added and 0.17 ml of pyridine was then added. After stirring at room temperature for 2 hours, 2% aqueous hydrochloric acid was poured into the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated aqueous sodium chloride solution, dried over magnesium sulfate, and then concentrated. The residue was subjected to silica gel column chromatography (eluent: hexane/ethyl acetate=5/1) to give 0.08 g of allyl [2-{2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-1,2,3,6-tetrahydropyrimidin-1-yl]phenoxy}phenoxy]acetate (compound a-21).

後処理

  1. additionwas added
  2. temperaturethe mixture was heated
  3. stirringstirred
  4. temperatureunder reflux for 2 hours
  5. waitAfter left
  6. temperaturefor cooling
  7. concentrationthe subsequent concentration
  8. dissolutionthe residue was dissolved in 3 ml of tetrahydrofuran (
  9. additionThen, 0.7 ml of tetrahydrofuran was added to 0.05 g of allyl alcohol, to which a third part of solution B
  10. additionwas added
  11. addition0.17 ml of pyridine was then added
  12. stirringAfter stirring at room temperature for 2 hours
  13. addition2% aqueous hydrochloric acid was poured into the reaction mixture
  14. extractionthe mixture was extracted with ethyl acetate
  15. washThe organic layer was washed with saturated aqueous sodium chloride solution
  16. dry with materialdried over magnesium sulfate
  17. concentrationconcentrated

出典と根拠

ORDレコード
ord-a70043193dde4b178fd319f71f7e8f4b
出典データセット
uspto-grants-2009_05
特許番号
US07538072B2

反応ノート

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