Water → (3,5-Dibromo-4-hydroxy-phenyl)-(2,3-dihydro-pyrido[2,3-b][1,4]oxazin-1-yl)-methanone

HRID 1943627노트

반응식

HRID 1943627 반응식
[Br:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([Br:12])[C:10]=1[OH:11])[C:5]([OH:7])=O.S(Cl)(Cl)=O.[NH:17]1[CH2:22][CH2:21][O:20][C:19]2[N:23]=[CH:24][CH:25]=[CH:26][C:18]1=2.O>CN(C)C(=O)C>[Br:12][C:9]1[CH:8]=[C:4]([C:5]([N:17]2[CH2:22][CH2:21][O:20][C:19]3[N:23]=[CH:24][CH:25]=[CH:26][C:18]2=3)=[O:7])[CH:3]=[C:2]([Br:1])[C:10]=1[OH:11]

참가 물질

6

반응물 4

HCID 962WaterHCID 24386Thionyl ChlorideHCID 768573,5-Dibromo-4-hydroxybenzoic acidHCID 151279021H,2H,3H-pyrido[2,3-b][1,4]oxazine

생성물 1

HCID 44610122(3,5-Dibromo-4-hydroxy-phenyl)-(2,3-dihydro-pyrido[2,3-b][1,4]oxazin-1-yl)-methanone수율 31%

시약·촉매·용매 1

HCID 31374Dimethylacetamide용매2회

실험 절차

3,5-dibromo-4-hydroxy-benzoic acid (65 mg, 0.22 mmol) was dissolved in N,N-dimethyl acetamide (1.5 ml) and then cooled to −5□. Thionyl chloride (0.024 ml, 0.33 mmol) was added thereto and stirred at −5□ for 30 minutes. 2,3-dihydro-1H-pyrido[2,3-b][1,4]oxazine dissolved in N,N-dimethyl acetamide (0.7 ml) was added thereto and then stirred at −5□ for 20 minutes, and subsequently stirred at room temperature for 15 hours. Water was added and the mixture was extracted with dichloromethane, and then the (extracted) combined organic layer was dried over anhydrous sodium sulfate (Na2SO4), filtered and evaporated under reduced pressure. The residue was purified by column chromatography on silica eluting with a solvent of n-hexane:ethyl acetate=1:1. The fractions containing the product were collected and evaporated to obtain pale-yellow solid (28 mg, 31%).

후처리

  1. temperaturecooled to −5□
  2. additionwas added
  3. stirringstirred at −5□ for 20 minutes
  4. stirringsubsequently stirred at room temperature for 15 hours
  5. extractionthe mixture was extracted with dichloromethane
  6. extractionthe (extracted)
  7. dry with materialwas dried over anhydrous sodium sulfate (Na2SO4)
  8. filtrationfiltered
  9. customevaporated under reduced pressure
  10. customThe residue was purified by column chromatography on silica eluting with a solvent of n-hexane
  11. additionThe fractions containing the product
  12. customwere collected
  13. customevaporated

출처 및 근거

ORD 기록
ord-28ef49d20cb3444d987b7537d0cfc5b2
출처 데이터셋
uspto-grants-2013_03
특허 번호
US08394792B2

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