Vinylene carbonate → 2-(4-Nitrobenzyl)oxazole

HRID 1508861

반응식

HRID 1508861 반응식
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([CH2:10][C:11]([NH2:13])=[O:12])=[CH:6][CH:5]=1)([O-:3])=[O:2].O1[CH:18]=[CH:17]OC1=O.CS(O)(=O)=O.O=P12OP3(OP(OP(O3)(O1)=O)(=O)O2)=O>>[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([CH2:10][C:11]2[O:12][CH:17]=[CH:18][N:13]=2)=[CH:8][CH:9]=1)([O-:3])=[O:2]

참가 물질

4

반응물 3

HCID 13385Vinylene carbonateHCID 2336132-(4-Nitrophenyl)acetamideHCID 86584057Phosphorus Pentoxide-Methanesulfonic Acid

생성물 1

HCID 901105832-(4-Nitrobenzyl)oxazole수율 25%

반응 조건

온도
100 °C

실험 절차

A mixture of 2-(4-nitrophenyl)acetamide (1.0 g, 5.55 mmol), 1,3-dioxol-2-one (0.955 g, 11.10 mmol), and Eaton's Reagent (9.9 g, 34.97 mmol) was heated to 100° C. overnight under a nitrogen atmosphere. After this time, the reaction was cooled, diluted with ice water, and extracted with ethyl acetate. The combined organic layer was dried over anhydrous sodium sulfate, filtered, and the filtrate was concentrated. The residue was purified by column chromatography (silica, dichloromethane/methanol) to afford the title compound (0.250 g, 25%). MW=204.18. 1H NMR (DMSO-d6, 500 MHz) δ 8.26-8.18 (m, 2H), 8.05 (d, J=0.8 Hz, 1H), 7.57 (d, J=8.8 Hz, 2H), 7.16 (s, 1H), 4.34 (s, 2H); APCI MS m/z 205 [M+H]+.

후처리

  1. temperatureAfter this time, the reaction was cooled
  2. extractionextracted with ethyl acetate
  3. dry with materialThe combined organic layer was dried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationthe filtrate was concentrated
  6. customThe residue was purified by column chromatography (silica, dichloromethane/methanol)

출처 및 근거

ORD 기록
ord-0cd4594167a24100aa1fe8653a3acc07
출처 데이터셋
uspto-grants-2015_12
특허 번호
US09221843B2

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