Water → 2-(2-Methylpropyl)thiazolo[4,5-c]quinoline

HRID 1838820

반응식

HRID 1838820 반응식
[NH2:1][C:2]1[CH:3]=[N:4][C:5]2[C:10]([C:11]=1[SH:12])=[CH:9][CH:8]=[CH:7][CH:6]=2.[C:13](O)(=O)[CH2:14][CH:15]([CH3:17])[CH3:16].O>ClCCl>[CH3:16][CH:15]([CH3:17])[CH2:14][C:13]1[S:12][C:11]2[C:10]3[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=3[N:4]=[CH:3][C:2]=2[N:1]=1

참가 물질

5

반응물 3

HCID 962WaterHCID 10430Isovaleric AcidHCID 1785079903-Aminoquinoline-4-thiol

생성물 1

HCID 226482712-(2-Methylpropyl)thiazolo[4,5-c]quinoline

시약·촉매·용매 1

HCID 6344Dichloromethane용매

반응 조건

온도
140 °C

실험 절차

3-Aminoquinoline-4-thiol (4.6 g) was added to polyphosphoric acid (80 g). Isovaleric acid (3.5 mL) was added and the reaction mixture was heated at 140° C. for 2 hours. The reaction mixture was poured into a mixture of ice and water (300 mL). The mixture was filtered through a layer of Celite® filter aid to remove some insoluble material. The filtrate was made alkaline with 50% sodium hydroxide while cooling with ice and then extracted with chloroform. The extract was washed with water, dried over magnesium sulfate and then concentrated under vacuum to provide an oil. The oil was dissolved in dichloromethane and then placed on a layer of silica gel and eluted with 1:1 ethyl acetate:hexanes. The eluant was concentrated under vacuum to provide 2-(2-methylpropyl)thiazolo[4,5-c]quinoline.

후처리

  1. filtrationThe mixture was filtered through a layer of Celite®
  2. filtrationfilter aid
  3. customto remove some insoluble material
  4. temperaturewhile cooling with ice
  5. extractionextracted with chloroform
  6. washThe extract was washed with water
  7. dry with materialdried over magnesium sulfate
  8. concentrationconcentrated under vacuum
  9. customto provide an oil
  10. washeluted with 1:1 ethyl acetate
  11. concentrationThe eluant was concentrated under vacuum

출처 및 근거

ORD 기록
ord-6e6d0e9add1642108b5dd0c05bc43edf
출처 데이터셋
uspto-grants-2004_01
특허 번호
US06677334B2

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