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 493925노트

반응식

HRID 493925 반응식
[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]

참가 물질

4

반응물 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

생성물 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

시약·촉매·용매 1

HCID 24386Thionyl Chloride용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-a70043193dde4b178fd319f71f7e8f4b
출처 데이터셋
uspto-grants-2009_05
특허 번호
US07538072B2

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