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

HRID 48270

반응식

HRID 48270 반응식
[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

참가 물질

7

반응물 3

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

생성물 1

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

시약·촉매·용매 3

HCID 962Water용매HCID 6344Dichloromethane용매HCID 12251Methoxyacetic Acid용매

반응 조건

온도
140 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-0795e61358bb43e2880c43b4130bad78
출처 데이터셋
uspto-grants-2004_03
특허 번호
US06703402B2

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