N-bromobutanimide → 5-Bromo-2-(bromomethyl)-1,3-benzothiazole

HRID 415623ノート

反応式

HRID 415623 の反応式
[Br:1]N1C(=O)CCC1=O.[Br:9][C:10]1[CH:11]=[CH:12][C:13]2[S:17][C:16]([CH3:18])=[N:15][C:14]=2[CH:19]=1>C(Cl)(Cl)(Cl)Cl>[Br:9][C:10]1[CH:11]=[CH:12][C:13]2[S:17][C:16]([CH2:18][Br:1])=[N:15][C:14]=2[CH:19]=1

参加物

4

反応物 2

HCID 67184N-bromobutanimideHCID 30174575-Bromo-2-methylbenzothiazole

生成物 1

HCID 144586425-Bromo-2-(bromomethyl)-1,3-benzothiazole収率 39%

試薬・触媒・溶媒 1

HCID 5943Carbon Tetrachloride溶媒

実験手順

N-Bromosuccinimide (4.45 g, 25 mmol, 1.4 equiv.) and subsequently α,α′azoisobutyronitrile (110 mg, 0.7 mmol, 0.04 equiv.) were added to a solution of 5-bromo-2-methyl-benzothiazole (4.07 g, 17.85 mmol, 1 equiv.) in CCl4 (110 ml). The reaction mixture was stirred at reflux for 24 hrs. After cooling, succinimide was removed by filtration and was rinsed with CCl4 (100 ml). The filtrate was evaporated to dryness under reduced pressure and the orange solid residue was purified by column chromatography on silica, eluted with CH2Cl2/hexane (20%-70% gradient), to give the desired product as a white solid, 2.15 g (39% yield). Mp 116-117, HPLC-MS (method 1): m/z 308 [M+H]+, Rt=4.84 min. The reaction gave also 1.40 g (20% yield) of the by-product 5-bromo-2-dibromomethyl-benzothiazole, as well as 0.89 g (22%) of un-reacted starting material.

後処理

  1. temperatureat reflux for 24 hrs
  2. temperatureAfter cooling
  3. customsuccinimide was removed by filtration
  4. washwas rinsed with CCl4 (100 ml)
  5. customThe filtrate was evaporated to dryness under reduced pressure
  6. customthe orange solid residue was purified by column chromatography on silica
  7. washeluted with CH2Cl2/hexane (20%-70% gradient)

出典と根拠

ORDレコード
ord-9301f0f2d9c54f0d837119e98be88953
出典データセット
uspto-grants-2012_01
特許番号
US08088791B2

反応ノート

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