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Phenyl isocyanate → (trans)-N-(7,8-Dihydro-7-hydroxy-6,6-dimethyl-6H-[1]benzopyrano[6,7-c][1,2,5]oxadiazol-8-yl)-N'-phenylurea

HRID 373680
ノート
印刷プレビュー

反応式

HRID 373680 の反応式
[CH3:1][C:2]1([CH3:17])[O:14][C:6]2=[CH:7][C:8]3[C:9]([CH:13]=[C:5]2[CH:4]([NH2:15])[CH:3]1[OH:16])=[N:10][O:11][N:12]=3.[C:18]1([N:24]=[C:25]=[O:26])[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>C(O)C.C(OC(C)C)(C)C>[OH:16][C@H:3]1[C@H:4]([NH:15][C:25]([NH:24][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[O:26])[C:5]2=[CH:13][C:9]3[C:8]([CH:7]=[C:6]2[O:14][C:2]1([CH3:17])[CH3:1])=[N:12][O:11][N:10]=3
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 7672Phenyl isocyanateHCID 11107308(+)-7,8-dihydro-6,6-dimethyl-7-hydroxy-8-amino-6H-pyrano[2,3-f]benz-2,1,3-oxadiazole

生成物 1

HCID 9819971(trans)-N-(7,8-Dihydro-7-hydroxy-6,6-dimethyl-6H-[1]benzopyrano[6,7-c][1,2,5]oxadiazol-8-yl)-N'-phenylurea収率 47.9%

試薬・触媒・溶媒 2

HCID 702Ethanol溶媒HCID 7914Diisopropyl Ether
溶媒

実験手順

To a solution of 7,8-dihydro-6,6-dimethyl-7-hydroxy-8-amino-6H-pyrano[2,3-f]benzo-2,1,3-oxadiazole (0.25 g, 1.06 mmoles) (prepared as described in part I of Example 1) in ethanol (2.5 ml) at 60° C. was added phenyl isocyanate (0.126 g, 1.06 mmoles). The reaction was heated at reflux for three hours, cooled to room temperature and diluted with isopropyl ether (5 ml). The product slowly crystallized from solution. It was collected via suction filtration and dried under vacuum to obtain 0.18 g of the desired compound as a beige solid. The residue obtained upon evaporation of the mother liquor was chromatographed on silica gel eluting with 1:1 ethyl acetate/hexane to afford an additional 0.16 g of product. The two crops were combined and triturated with isopropyl ether to obtain 0.30 g of the title compound as an off-white solid (m.p. 215°-216° C.).

後処理

  1. temperatureThe reaction was heated
  2. temperatureat reflux for three hours
  3. customThe product slowly crystallized from solution
  4. filtrationIt was collected via suction filtration
  5. customdried under vacuum

出典と根拠

ORDレコード
ord-902cc5270e364a738f5cec5eec8abfd3
出典データセット
uspto-grants-1992_11
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05164509

反応ノート

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