Sodium Carbonate → 2-(4-Diethylcarbamoylphenyl)anisole

HRID 895619노트

반응식

HRID 895619 반응식
[CH2:1]([N:3]([CH2:13][CH3:14])[C:4]([C:6]1[CH:11]=[CH:10][C:9](I)=[CH:8][CH:7]=1)=[O:5])[CH3:2].[CH3:15][O:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1OB(O)O.C(=O)([O-])[O-].[Na+].[Na+]>C(COC)OC.C1(C)C=CC=CC=1.O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH2:1]([N:3]([CH2:13][CH3:14])[C:4]([C:6]1[CH:11]=[CH:10][C:9]([C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=2[O:16][CH3:15])=[CH:8][CH:7]=1)=[O:5])[CH3:2]

참가 물질

8

반응물 3

HCID 10340Sodium CarbonateHCID 875218N,N-diethyl-4-iodobenzamideHCID 21940032(2-Methoxyphenyl)boric acid

생성물 1

HCID 223807362-(4-Diethylcarbamoylphenyl)anisole수율 88%

시약·촉매·용매 4

HCID 178418397HCID 178418397, 화합물촉매HCID 962Water용매2회HCID 1140Toluene용매HCID 80711,2-Dimethoxyethane용매

실험 절차

4-Diethylcarbamoyl-1-iodobenzene (100 mg) was dissolved in dimethoxyethane (1 ml), added with tetrakis(triphenylphosphine)palladium (19.1 mg) under argon atmosphere, and stirred at room temperature for 10 minutes. The reaction mixture was added with the solution of (2-methoxyphenyl)boric acid (100 mg) dissolved in toluene (0.5 ml) prepared above and a solution of sodium carbonate (105 mg) dissolved in water (0.5 ml) and stirred at 90° C. for 5.5 hours. The reaction mixture was added with water (2 ml) and extracted twice with dichloromethane (4 ml). The organic layer was dried over anhydrous magnesium sulfate, and then the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (elution solvent: hexane:ethyl acetate=3:1) to obtain 81.9 mg of the title compound. Yield: 88%.

후처리

  1. stirringstirred at 90° C. for 5.5 hours
  2. extractionextracted twice with dichloromethane (4 ml)
  3. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (elution solvent: hexane:ethyl acetate=3:1)

출처 및 근거

ORD 기록
ord-8b08b9782b2c4ddf9b3feaf5b6da48e7
출처 데이터셋
uspto-grants-2005_07
특허 번호
US06916822B2

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