2-Bromo-1-(3-nitrophenyl)ethan-1-one → Ethyl 1-[4-(3-nitrophenyl)-1,3-thiazol-2-yl]piperidine-4-carboxylate

HRID 1028146노트

반응식

HRID 1028146 반응식
Br[CH2:2][C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([N+:11]([O-:13])=[O:12])[CH:6]=1)=O.[C:14]([N:17]1[CH2:22][CH2:21][CH:20]([C:23]([O:25][CH2:26][CH3:27])=[O:24])[CH2:19][CH2:18]1)(=[S:16])[NH2:15]>C(O)C>[N+:11]([C:7]1[CH:6]=[C:5]([C:3]2[N:15]=[C:14]([N:17]3[CH2:22][CH2:21][CH:20]([C:23]([O:25][CH2:26][CH3:27])=[O:24])[CH2:19][CH2:18]3)[S:16][CH:2]=2)[CH:10]=[CH:9][CH:8]=1)([O-:13])=[O:12]

참가 물질

4

반응물 2

HCID 752132-Bromo-1-(3-nitrophenyl)ethan-1-oneHCID 23076419Ethyl 1-carbamothioylpiperidine-4-carboxylate

생성물 1

HCID 71075037Ethyl 1-[4-(3-nitrophenyl)-1,3-thiazol-2-yl]piperidine-4-carboxylate수율 54.5%

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

A solution of 2-bromo-1-(3-nitrophenyl)ethanone (621 mg, 2.54 mmol) and ethyl 1-carbamothioylpiperidine-4-carboxylate (500 mg, 2.31 mmol) in ethanol (7.7 mL) was heated to reflux for 16 hours, and then cooled to room temperature. The mixture was concentrated under reduced pressure and the resulting residue purified directly by CombiFlash (0-70% ethyl acetate/hexanes) to provide 457 mg (1.26 mmol, 49% yield) of ethyl 1-[4-(3-nitrophenyl)-1,3-thiazol-2-yl]piperidine-4-carboxylate as a yellow solid.

후처리

  1. temperatureto reflux for 16 hours
  2. concentrationThe mixture was concentrated under reduced pressure
  3. customthe resulting residue purified directly by CombiFlash (0-70% ethyl acetate/hexanes)

출처 및 근거

ORD 기록
ord-a514779c524146dab3ad63b0f32f9037
출처 데이터셋
uspto-grants-2014_05
특허 번호
US08735417B2

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