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

HRID 1028146ノート

反応式

HRID 1028146 の反応式
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]

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-a514779c524146dab3ad63b0f32f9037
出典データセット
uspto-grants-2014_05
特許番号
US08735417B2

反応ノート

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