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

HRID 393928

反応式

HRID 393928 の反応式
[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
140 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-66330b6bd7924606a8c4cf14302404bc
出典データセット
uspto-grants-2004_10
特許番号
US06809203B2

関連ノート

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