Sodium Hydroxide → 2-(Methoxymethyl)thiazolo[4,5-c]quinoline

HRID 1872616

反応式

HRID 1872616 の反応式
[CH3:1][O:2][CH2:3][C:4](Cl)=O.[NH2:7][C:8]1[CH:9]=[N:10][C:11]2[C:16]([C:17]=1[SH:18])=[CH:15][CH:14]=[CH:13][CH:12]=2.[OH-].[Na+]>COCC(O)=O.O.ClCCl>[CH3:1][O:2][CH2:3][C:4]1[S:18][C:17]2[C:16]3[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=3[N:10]=[CH:9][C:8]=2[N:7]=1

参加物

7

反応物 3

HCID 14798Sodium HydroxideHCID 96623Methoxyacetyl chlorideHCID 1785079903-Aminoquinoline-4-thiol

生成物 1

HCID 226482592-(Methoxymethyl)thiazolo[4,5-c]quinoline

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 6344Dichloromethane溶媒HCID 12251Methoxyacetic Acid溶媒

反応条件

温度
140 °C

実験手順

Methoxyacetyl chloride (1.8 mL) was added to a mixture of 3-aminoquinoline-4-thiol (2.8 g) in methoxyacetic acid (15 mL). The reaction was heated at about 140° C. for 1 hour and then allowed to cool to ambient temperature. The reaction mixture was diluted with a small amount of water, made basic with 10% sodium hydroxide and then extracted with dichloromethane (300 mL). The extract was washed with sodium bicarbonate, washed with water, dried over magnesium sulfate and then concentrated under vacuum to provide crude product as a dark oil. The oil was dissolved in dichloromethane and then placed on a layer of silica gel. The silica gel was eluted with 1:1 hexane:ethyl acetate. The eluant was concentrated under vacuum to provide 2.3 g of 2-(methoxymethyl)thiazolo[4,5-c]quinoline as an orange solid.

後処理

  1. temperatureto cool to ambient temperature
  2. extractionextracted with dichloromethane (300 mL)
  3. washThe extract was washed with sodium bicarbonate
  4. washwashed with water
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated under vacuum
  7. customto provide crude product as a dark oil
  8. washThe silica gel was eluted with 1:1 hexane
  9. concentrationThe eluant was concentrated under vacuum

出典と根拠

ORDレコード
ord-a94be06398884aec818d280157bfbf50
出典データセット
uspto-grants-2000_08
特許番号
US06110929

関連ノート

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