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Cesium carbonate → HCID 18991734, 화합물

HRID 376061
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HRID 376061 반응식
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([N:10]([CH:14]([CH3:16])[CH3:15])[CH:11]([CH3:13])[CH3:12])=[O:9])=[CH:4][C:3]=1[O:17][CH3:18].C(=O)([O-])[O-].[Cs+].[Cs+].Br[CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][O:31][C:32]1[CH:37]=[CH:36][C:35]([C:38](=[NH:42])[O:39][CH2:40][CH3:41])=[CH:34][CH:33]=1>CN(C)C=O>[CH3:18][O:17][C:3]1[CH:4]=[C:5]([C:8]([N:10]([CH:11]([CH3:12])[CH3:13])[CH:14]([CH3:16])[CH3:15])=[O:9])[CH:6]=[CH:7][C:2]=1[O:1][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][O:31][C:32]1[CH:33]=[CH:34][C:35]([C:38](=[NH:42])[O:39][CH2:40][CH3:41])=[CH:36][CH:37]=1
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 3

HCID 10796Cesium carbonateHCID 18991675HCID 18991675, 화합물HCID 217472594-Hydroxy-3-methoxy-N,N-di(propan-2-yl)benzamide

생성물 1

HCID 18991734HCID 18991734, 화합물

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
70 °C

실험 절차

A stirred solution of 4-hydroxy-3-methoxy-N,N-bis(1-methylethyl)benzenecarboxamide (319 mg, 1.27 mmol) in 3.5 mL anhydrous N,N-dimethylformamide is treated with cesium carbonate (435 mg, 1.33 mmol) and ethyl 4-[5-bromopentoxy]benzenecarboximidoate (400 mg, 1.27 mmol) and heated at 70° C. for 1.0 hours. After cooling to room temperature, the reaction is partitioned between ethyl acetate and water and the organics washed with brine, dried over sodium sulfate and concentrated in vacuo to afford a yellow oil. This material is purified by chromatography on silica gel (22 g) with 30-75% ethyl acetate/hexanes as the eluent to afford ethyl 4-[5-[2-methoxy-4-[N,N-bis(1-methylethyl)aminocarbonyl]phenoxy]pentoxy]benzenecarboximidoate as a colorless oil.

후처리

  1. temperatureAfter cooling to room temperature
  2. customthe reaction is partitioned between ethyl acetate and water
  3. washthe organics washed with brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customto afford a yellow oil
  7. customThis material is purified by chromatography on silica gel (22 g) with 30-75% ethyl acetate/hexanes as the eluent

출처 및 근거

ORD 기록
ord-bba568bde14a4a99bea20e7060532139
출처 데이터셋
uspto-grants-1996_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05488160

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