Lithium Hydroxide → 2-(Pyridin-2-yl)-1,3-thiazole-5-carboxylic acid

HRID 1260322노트

반응식

HRID 1260322 반응식
C[O:2][C:3]([C:5]1[S:9][C:8]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][N:11]=2)=[N:7][CH:6]=1)=[O:4].[OH-].[Li+].ClCCl>C1COCC1.CO>[N:11]1[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=1[C:8]1[S:9][C:5]([C:3]([OH:4])=[O:2])=[CH:6][N:7]=1

참가 물질

5

반응물 3

HCID 3939Lithium HydroxideHCID 6344DichloromethaneHCID 57688443Methyl 2-(pyridin-2-yl)thiazole-5-carboxylate

생성물 1

HCID 232838552-(Pyridin-2-yl)-1,3-thiazole-5-carboxylic acid수율 93.9%

시약·촉매·용매 1

HCID 21899815MeOH tetrahydrofuran용매

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온도
0 °C

실험 절차

2-Pyridin-2-yl-thiazol-5-carboxylic acid methyl ester (0.34 g, 1.55 mmol) was dissolved in a THF/methanol (5 ml/1 ml) mixture, cooled to 0° C. and treated with lithium hydroxide (4.7 ml, 1N aqueous solution). The reaction mixture was allowed to warm-up to ambient temperature, stirred at that temperature for 30 min and the pH value was subsequently adjusted to ˜5. The resulting suspension was treated with dichloromethane (50 ml) and filtered. The precipitate was washed with water and dichloromethane, the filtrate was extracted with dichloromethane. The combined organic phases were dried, evaporated and combined with the precipitate to yield the product as light brown solid (0.3 g, 92%). MS: M=161.1 (M-CO2—H)−

후처리

  1. temperatureto warm-up to ambient temperature
  2. filtrationfiltered
  3. washThe precipitate was washed with water and dichloromethane
  4. extractionthe filtrate was extracted with dichloromethane
  5. customThe combined organic phases were dried
  6. customevaporated

출처 및 근거

ORD 기록
ord-2b032ecaf5f24dff94b6e06c1c1b144d
출처 데이터셋
uspto-grants-2013_06
특허 번호
US08470820B2

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