Sulfuric Acid → N-[2-(2-Methyl-6H-indeno[5,4-d][1,3]oxazol-8-yl)ethyl]acetamide

HRID 340703노트

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HRID 340703 반응식
[CH3:1][C:2]1[O:3][C:4]2[C:13]3[C:12](=[CH:14][CH2:15][NH:16][C:17](=[O:19])[CH3:18])[CH2:11][CH2:10][C:9]=3[CH:8]=[CH:7][C:5]=2[N:6]=1.S(=O)(=O)(O)O.C(=O)([O-])O.[Na+]>C1(C)C=CC=CC=1>[CH3:1][C:2]1[O:3][C:4]2[C:13]3[C:12]([CH2:14][CH2:15][NH:16][C:17](=[O:19])[CH3:18])=[CH:11][CH2:10][C:9]=3[CH:8]=[CH:7][C:5]=2[N:6]=1

참가 물질

5

반응물 3

HCID 1118Sulfuric AcidHCID 516892Sodium BicarbonateHCID 67354710N-[2-(2-Methyl-6,7-dihydro-8H-indeno[5,4-d][1,3]oxazol-8-ylidene)ethyl]acetamide

생성물 1

HCID 23725512N-[2-(2-Methyl-6H-indeno[5,4-d][1,3]oxazol-8-yl)ethyl]acetamide수율 63%

시약·촉매·용매 1

HCID 1140Toluene용매

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온도
100 °C

실험 절차

N-[2-(2-Methyl-6,7-dihydro-8H-indeno[5,4-d][1,3]oxazol-8-ylidene)ethyl]acetamide (63.5 mg, 0.248 mmol) was dissolved in toluene (2.5 mL), sulfuric acid (24.3 μL, 0.248 mmol) was added, and the mixture was stirred at 100° C. for 5 hr. To the reaction solution was added saturated aqueous sodium hydrogencarbonate solution. The mixture was extracted with ethyl acetate and washed with saturated brine. The solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/methanol=100/0→90/10) to give the title compound (40.0 mg, yield 63%).

후처리

  1. extractionThe mixture was extracted with ethyl acetate
  2. washwashed with saturated brine
  3. customThe solvent was evaporated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (ethyl acetate/methanol=100/0→90/10)

출처 및 근거

ORD 기록
ord-3d2c8d98e8b14bfea76a5c2a19aa713d
출처 데이터셋
uspto-grants-2014_11
특허 번호
US08895591B2

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