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

HRID 842095
ノート
印刷プレビュー

反応式

HRID 842095 の反応式
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
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 2

HCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 22618278N-(2-hydroxy-3-nitrophenyl)-3-cyclopentyloxy-4-methoxyphenylacetamide

生成物 1

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

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 7237O-Xylene溶媒

実験手順

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.).

後処理

  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))

出典と根拠

ORDレコード
ord-eb3593b26aae4ac69d398faf77be4b96
出典データセット
uspto-grants-2002_04
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06372770B1

反応ノート

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