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Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1) → 2-(3-Cyclopentyloxy-4-methoxybenzyl)-7-nitrobenzoxazole

HRID 842095
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HRID 842095 반응식
O[C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[CH:4][C:3]=1[NH:11][C:12](=[O:28])[CH2:13][C:14]1[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[C:16]([O:22][CH:23]2[CH2:27][CH2:26][CH2:25][CH2:24]2)[CH:15]=1.C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1>C1(C)C(C)=CC=CC=1.O>[CH:23]1([O:22][C:16]2[CH:15]=[C:14]([CH:19]=[CH:18][C:17]=2[O:20][CH3:21])[CH2:13][C:12]2[O:28][C:2]3[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[CH:4][C:3]=3[N:11]=2)[CH2:24][CH2:25][CH2:26][CH2:27]1
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HCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 22618278N-(2-hydroxy-3-nitrophenyl)-3-cyclopentyloxy-4-methoxyphenylacetamide

생성물 1

HCID 101095852-(3-Cyclopentyloxy-4-methoxybenzyl)-7-nitrobenzoxazole수율 58.1%

시약·촉매·용매 2

HCID 962Water용매HCID 7237O-Xylene용매

실험 절차

A solution of N-(2-hydroxy-3-nitrophenyl)-3-cyclopentyloxy-4-methoxy-phenylacetamide (2.0 g) and pyridinium p-toluene-sulphonate (500 mg) in xylene (140 ml) was heated at reflux, under nitrogen, overnight. The reaction mixture was cooled to room temperature, diluted with water (100 ml) and extracted with dichloro-methane (3×75 ml). The combined organic extracts were washed with water (3×100 ml), brine (100 ml), dried (CaSO4) and evaporated in-vacuo to yield an orange oil. The oil was purified by flash chromatography (SiO2; dichloromethane; ethanol; ammonia (50:1:0.1)) to yield the title compound (1.107 g, 58%) as an orange solid (mp 95-98.5° C.).

후처리

  1. temperatureat reflux, under nitrogen, overnight
  2. extractionextracted with dichloro-methane (3×75 ml)
  3. washThe combined organic extracts were washed with water (3×100 ml), brine (100 ml)
  4. dry with materialdried (CaSO4)
  5. customevaporated in-vacuo
  6. customto yield an orange oil
  7. customThe oil was purified by flash chromatography (SiO2; dichloromethane; ethanol; ammonia (50:1:0.1))

출처 및 근거

ORD 기록
ord-eb3593b26aae4ac69d398faf77be4b96
출처 데이터셋
uspto-grants-2002_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06372770B1

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