N-bromobutanimide → 3-(Bromomethyl)-6-phenylpyridazine

HRID 241276

反応式

HRID 241276 の反応式
[CH3:1][C:2]1[N:3]=[N:4][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[CH:6][CH:7]=1.C1C(=O)N([Br:21])C(=O)C1.N(C(C)(CC(C)C)C#N)=NC(C)(CC(C)C)C#N>ClCCCl>[Br:21][CH2:1][C:2]1[N:3]=[N:4][C:5]([C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=2)=[CH:6][CH:7]=1

参加物

5

反応物 3

HCID 67184N-bromobutanimideHCID 915372,2'-Azobis(2,4-dimethylvaleronitrile)2 回HCID 113787443-Methyl-6-phenylpyridazine

生成物 1

HCID 667174453-(Bromomethyl)-6-phenylpyridazine収率 33.2%

試薬・触媒・溶媒 1

HCID 111,2-Dichloroethane溶媒

反応条件

温度
80 °C

実験手順

To a solution of 3-methyl-6-phenylpyridazine (925 mg, 5.43 mmol) in 1,2-dichloroethane (28 ml) were added NBS (1.07 g, 6.01 mmol) and 2,2′-azobis(2,4-dimethylvaleronitrile) (67.3 mg, 0.271 mmol), followed by stirring at 80° C. for 1 hour. During the reaction, 2,2′-azobis(2,4-dimethylvaleronitrile)(134 mg, 0.540 mmol) was additionally added in two portions. After completion of the reaction, the reaction solution was concentrated under reduced pressure. The resulting residue was subjected to silica gel column chromatography (eluent; hexane:ethyl acetate=5:1→0:1 (V/V)), and fractions containing the desired compound were concentrated under reduced pressure to afford the title compound (449 mg) as a slightly brown solid. (Yield: 33%)

後処理

  1. additionwas additionally added in two portions
  2. customAfter completion of the reaction
  3. concentrationthe reaction solution was concentrated under reduced pressure
  4. additioncontaining the desired compound
  5. concentrationwere concentrated under reduced pressure

出典と根拠

ORDレコード
ord-9764fadbf8674d9f85871f740dd60b76
出典データセット
uspto-grants-2014_02
特許番号
US08648097B2

関連ノート

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