N-bromobutanimide → HCID 45117088、化合物

HRID 2388147ノート

反応式

HRID 2388147 の反応式
[CH2:1]([O:3][C:4]([C:6]1[C:7]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[N:8][O:9][C:10]=1[CH3:11])=[O:5])[CH3:2].[Br:18]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>[CH2:1]([O:3][C:4]([C:6]1[C:7]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[N:8][O:9][C:10]=1[CH2:11][Br:18])=[O:5])[CH3:2]

参加物

5

反応物 2

HCID 67184N-bromobutanimideHCID 70838Ethyl 5-methyl-3-phenylisoxazole-4-carboxylate

生成物 1

HCID 45117088HCID 45117088、化合物収率 102,372%

試薬・触媒・溶媒 2

HCID 7187Benzoyl Peroxide触媒HCID 5943Carbon Tetrachloride溶媒

実験手順

A mixture of 5-methyl-3-phenyl-isoxazole-4-carboxylic acid ethyl ester (5.02 g, 0.02 mol), N-bromosuccinimide (4.06 g, 0.02 mmol) and benzoyl peroxide (263 mg, 1.09 mmol) in carbon tetrachloride (80 ml) was refluxed for 20 h before it was cooled to room temperature and partitioned between dichloromethane and water. The organic layer was washed with saturated aqueous sodium bicarbonate solution, and brine before it was dried over anhydrous sodium sulfate and concentrated in vacuo to give the crude title compound as a yellow oil (6.35 g) that was used in the following step without further purification: 1H NMR (CDCl3, 200 MHz): δ=7.61 (m, 2H), 7.43 (m, 3H), 4.80 (s, 2H), 4.25 (q, J=7.0 Hz, 2H), 1.26 (t, J=7.0 Hz, 3H).

後処理

  1. temperaturewas refluxed for 20 h before it
  2. custompartitioned between dichloromethane and water
  3. washThe organic layer was washed with saturated aqueous sodium bicarbonate solution, and brine before it
  4. dry with materialwas dried over anhydrous sodium sulfate
  5. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-6db46bf246264ba4918a117270591212
出典データセット
uspto-grants-2012_09
特許番号
US08269008B2

反応ノート

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