Ammonium Hydroxide → Ethyl 2-(piperidin-4-yl)-1,3-thiazole-5-carboxylate

HRID 715804

반응식

HRID 715804 반응식
C(O[CH:4]=[CH:5][C:6]([O:8][CH2:9][CH3:10])=[O:7])C.BrN1C(=O)CCC1=O.[C:19]([CH:22]1[CH2:27][CH2:26][N:25](C(OC(C)(C)C)=O)[CH2:24][CH2:23]1)(=[S:21])[NH2:20].[OH-].[NH4+]>O1CCOCC1.O>[NH:25]1[CH2:26][CH2:27][CH:22]([C:19]2[S:21][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:4][N:20]=2)[CH2:23][CH2:24]1

참가 물질

6

반응물 4

HCID 14923Ammonium HydroxideHCID 67184N-bromobutanimideHCID 221780Ethyl 3-ethoxy-2-propenoateHCID 2735648tert-Butyl 4-carbamothioylpiperidine-1-carboxylate

생성물 1

HCID 86701983Ethyl 2-(piperidin-4-yl)-1,3-thiazole-5-carboxylate

시약·촉매·용매 1

HCID 218864351,4-Dioxane--water (1/1)용매

반응 조건

온도
-10 °C

실험 절차

Ethyl 3-ethoxyacrylate (1.50 g, 10.38 mml) was dissolved in dioxane/water and chilled to −10° C. N-Bromosuccinimide (2.03 g, 11.42 mmol) was added and the mixture was stirred 1 hour at room temperature. tert-Butyl 4-carbamothioylpiperidine-1-carboxylate (2.54 g, 10.38 mmol) was added and the mixture was heated at 100° C. for 1 hour. The reaction mixture was poured into 25 mL saturated ammonium hydroxide and extracted with dichloromethane. The combined organic layers were washed with brine, dried with sodium sulfate, filtered, and concentrated. Normal phase chromatography provided the title compound.

후처리

  1. temperaturethe mixture was heated at 100° C. for 1 hour
  2. extractionextracted with dichloromethane
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried with sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

출처 및 근거

ORD 기록
ord-329f3457c78540efbaeee55cee310da5
출처 데이터셋
uspto-grants-2015_11
특허 번호
US09187472B2

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