Isopropylamine → 2-Chloro-thiazole-5-carboxylic acid isopropylamide

HRID 1923645노트

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HRID 1923645 반응식
[CH:1]([NH2:4])([CH3:3])[CH3:2].C[Al](C)C.C([O:11][C:12]([C:14]1[S:18][C:17]([Cl:19])=[N:16][CH:15]=1)=O)C>O1CCOCC1.C1(C)C=CC=CC=1>[CH:1]([NH:4][C:12]([C:14]1[S:18][C:17]([Cl:19])=[N:16][CH:15]=1)=[O:11])([CH3:3])[CH3:2]

참가 물질

6

반응물 3

HCID 6363IsopropylamineHCID 16682925TrimethylaluminumHCID 19017727Ethyl 2-chloro-1,3-thiazole-5-carboxylate

생성물 1

HCID 666437382-Chloro-thiazole-5-carboxylic acid isopropylamide수율 94%

시약·촉매·용매 2

HCID 1140Toluene용매HCID 312751,4-Dioxane용매2회

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온도
90 °C

실험 절차

To a stirred solution of isopropylamine (123 mg, 2.08 mmol) in dioxane (5 mL) under argon and at room temperature was added trimethylaluminium (1.04 mL of a 2M solution in toluene, 2.08 mmol). After 1 h, a solution of 2-chloro-thiazole-5-carboxylic acid ethyl ester (100 mg, 0.522 mmol) in dioxane (5 mL) was added and the reaction mixture warmed to 90° C. After 6 h, the reaction mixture was cooled, quenched with Seignettes's salt solution and water, then extracted with dichloromethane. The combined organic extracts were dried, filtered and concentrated. Purification by chromatography (silica, 0 to 30% ethyl acetate in heptane) gave the title compound (100 mg, 94%) as a white solid. MS: m/e=203.4 [M+H]+.

후처리

  1. waitAfter 6 h
  2. temperaturethe reaction mixture was cooled
  3. customquenched with Seignettes's salt solution and water
  4. extractionextracted with dichloromethane
  5. customThe combined organic extracts were dried
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customPurification by chromatography (silica, 0 to 30% ethyl acetate in heptane)

출처 및 근거

ORD 기록
ord-20cf030f0bec4b029a833ced77cbe858
출처 데이터셋
uspto-grants-2012_05
특허 번호
US08178522B2

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