N-bromobutanimide → 4-(Bromomethyl)-2,1,3-benzothiadiazole

HRID 843243

反応式

HRID 843243 の反応式
[CH3:1][C:2]1[C:10]2[C:6](=[N:7][S:8][N:9]=2)[CH:5]=[CH:4][CH:3]=1.[Br:11]N1C(=O)CCC1=O.CCCCCC.C(OCC)(=O)C>C(Cl)(Cl)(Cl)Cl>[Br:11][CH2:1][C:2]1[C:10]2[C:6](=[N:7][S:8][N:9]=2)[CH:5]=[CH:4][CH:3]=1

参加物

5

反応物 3

HCID 67184N-bromobutanimideHCID 27812624-Methyl-2,1,3-benzothiadiazoleHCID 21226206Ethyl acetate hexane

生成物 1

HCID 27762864-(Bromomethyl)-2,1,3-benzothiadiazole

試薬・触媒・溶媒 1

HCID 5943Carbon Tetrachloride溶媒

実験手順

A mixture of 4-methyl-2,1,3-benzothiadiazole (6.0 g, 40 mmol) and N-bromosuccinimide (7.12 g, 40 mmol) in carbon tetrachloride (80 mL) was refluxed under irradiation with a sunlamp for 8 hours. After cooling with ice-water bath, the succinimide was filtered off and the filtrate was washed with saturated Na2S2O3, brine, dried over Na2SO4. After removal of solvent pure 4-bromomethyl-2,1,3-benzothiadiazole (8.8 g, 96%) was obtained as a light-yellow crystalline powder. Rf=0.45 (hexane/ethyl acetate=4:1); 1H NMR (200 MHz, CDCl3) δ5.00 (s, 2H), 7.57 (m, 2H), 7.98 (d, J1=8.5 Hz, J2=1.2 Hz, 1H); HRMS: Calcd. for C7H5BrN2S 227.9357, found 227.9395.

後処理

  1. temperaturewas refluxed under irradiation with a sunlamp for 8 hours
  2. temperatureAfter cooling with ice-water bath
  3. filtrationthe succinimide was filtered off
  4. washthe filtrate was washed with saturated Na2S2O3, brine
  5. dry with materialdried over Na2SO4
  6. customAfter removal of solvent pure 4-bromomethyl-2,1,3-benzothiadiazole (8.8 g, 96%)
  7. customwas obtained as a light-yellow crystalline powder

出典と根拠

ORDレコード
ord-c89231210ee646d59780ed56e84ac4ac
出典データセット
uspto-grants-2002_04
特許番号
US06376664B1

関連ノート

読み込み中…