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 433694ノート

反応式

HRID 433694 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].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]

参加物

4

反応物 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

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

実験手順

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].

後処理

  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

出典と根拠

ORDレコード
ord-ef6bdf6a29bf40ddacbe3a16bb0f42b5
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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