Benzoyl Peroxide → HCID 21866262、化合物

HRID 857784ノート

反応式

HRID 857784 の反応式
[Cl:1][C:2]1[C:6]([C:7]2[CH:12]=[CH:11][C:10]([Cl:13])=[CH:9][C:8]=2[CH3:14])=[N:5][S:4][N:3]=1.C1C(=O)N([Br:22])C(=O)C1.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl>[Br:22][CH2:14][C:8]1[CH:9]=[C:10]([Cl:13])[CH:11]=[CH:12][C:7]=1[C:6]1[C:2]([Cl:1])=[N:3][S:4][N:5]=1

参加物

5

反応物 3

HCID 7187Benzoyl Peroxide2 回HCID 67184N-bromobutanimideHCID 21866306HCID 21866306、化合物

生成物 1

HCID 21866262HCID 21866262、化合物

試薬・触媒・溶媒 1

HCID 5943Carbon Tetrachloride溶媒

実験手順

A mixture of 3-chloro-4-(4-chloro-2-methylphenyl)-1,2,5-thiadiazole (0.211 g, 0.86 mmol), NBS (0.153 g, 0.86 mmol) and benzoyl peroxide (10.4 mg, 0.04 mmol) in carbon tetrachloride (5.0 mL) were refluxed for 1 h. More benzoyl peroxide (10.4 mg, 0.04 mmol) was added and the solution was refluxed for a further 16 h. The resulting suspension was filtered, rinsing with ether. The filtrate was washed with 10% aqueous sodium sulfite, saturated aqueous sodium bicarbonate solution and brine. The ether layer was separated, dried (Na2SO4) and reduced in vacuo. The residue was purified by flash chromatography on silica (eluting with EtOAc/hexanes gradient, 1–3% EtOAc). 3-[2-(Bromomethyl)-4-chlorophenyl]-4-chloro-1,2,5-thiadiazole was isolated as a yellow oil. 1H NMR (CDCl3, 400 MHz) δ 4.51 (s, 2H), 7.43 (s, 2H), 7.55 (s, 1H).

後処理

  1. temperaturewere refluxed for 1 h
  2. temperaturethe solution was refluxed for a further 16 h
  3. filtrationThe resulting suspension was filtered
  4. washrinsing with ether
  5. washThe filtrate was washed with 10% aqueous sodium sulfite, saturated aqueous sodium bicarbonate solution and brine
  6. customThe ether layer was separated
  7. dry with materialdried (Na2SO4)
  8. customThe residue was purified by flash chromatography on silica (eluting with EtOAc/hexanes gradient, 1–3% EtOAc)

出典と根拠

ORDレコード
ord-51e9ef4e601840eabeeb99cdb14b040e
出典データセット
uspto-grants-2006_12
特許番号
US07144899B2

反応ノート

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