Benzoyl Peroxide → HCID 21866262, 화합물

HRID 857784노트

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HRID 857784 반응식
[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

참가 물질

5

반응물 3

HCID 7187Benzoyl Peroxide2회HCID 67184N-bromobutanimideHCID 21866306HCID 21866306, 화합물

생성물 1

HCID 21866262HCID 21866262, 화합물

시약·촉매·용매 1

HCID 5943Carbon Tetrachloride용매

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-51e9ef4e601840eabeeb99cdb14b040e
출처 데이터셋
uspto-grants-2006_12
특허 번호
US07144899B2

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