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 433694노트

반응식

HRID 433694 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].S(Cl)(Cl)=O.O1C[CH2:41][CH2:40][CH2:39]1>>[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][CH2:41][CH:40]=[CH2:39])=[O:10]

참가 물질

4

반응물 3

HCID 8028TetrahydrofuranHCID 24386Thionyl ChlorideHCID 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

실험 절차

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 was dissolved in tetrahydrofuran, to this was added 0.7 ml of thionyl chloride while stirring, then, the mixture was heated while stirring under reflux condition for 2 hours. Then, the solution was allowed to cool, concentrated, then, dissolved in 3 ml of tetrahydrofuran (hereinafter, referred to as Solution B). 0.7 ml of tetrahydrofuran was added to 0.05 g of allyl alcohol, and trisected portions of Solution B were added, then, 0.17 ml of pyridine was added. The mixture was stirred for 2 hours at room temperature, then, 2% aqueous hydrochloric acid was poured into the reaction solution, and extracted with ethyl acetate. The organic layer was washed with saturated saline, and dried over magnesium sulfate, then, concentrated. The residue was subjected to silica gel column chromatography (eluent: hexane/ethyl acetate=5/1) to obtain 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 3-20 of the present invention].

후처리

  1. temperaturethe mixture was heated
  2. stirringwhile stirring
  3. temperatureunder reflux condition for 2 hours
  4. temperatureto cool
  5. concentrationconcentrated
  6. dissolutiondissolved in 3 ml of tetrahydrofuran (hereinafter,
  7. addition0.7 ml of tetrahydrofuran was added to 0.05 g of allyl alcohol
  8. additionwere added
  9. addition0.17 ml of pyridine was added
  10. stirringThe mixture was stirred for 2 hours at room temperature
  11. addition2% aqueous hydrochloric acid was poured into the reaction solution
  12. extractionextracted with ethyl acetate
  13. washThe organic layer was washed with saturated saline
  14. dry with materialdried over magnesium sulfate
  15. concentrationconcentrated

출처 및 근거

ORD 기록
ord-ef6bdf6a29bf40ddacbe3a16bb0f42b5
출처 데이터셋
uspto-grants-2003_12
특허 번호
US06667413B2

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