1,3-Dibromo-5,5-dimethylhydantoin → 2-(1-Bromoethyl)-3,5-dichloroquinoxaline

HRID 1019809노트

반응식

HRID 1019809 반응식
[Cl:1][C:2]1[C:3]([CH2:13][CH3:14])=[N:4][C:5]2[C:10]([N:11]=1)=[C:9]([Cl:12])[CH:8]=[CH:7][CH:6]=2.[Br:15]N1C(C)(C)C(=O)N(Br)C1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl>[Br:15][CH:13]([C:3]1[C:2]([Cl:1])=[N:11][C:10]2[C:5](=[CH:6][CH:7]=[CH:8][C:9]=2[Cl:12])[N:4]=1)[CH3:14]

참가 물질

5

반응물 3

HCID 64791,3-Dibromo-5,5-dimethylhydantoinHCID 7187Benzoyl PeroxideHCID 866985103,5-Dichloro-2-ethylquinoxaline

생성물 1

HCID 866985112-(1-Bromoethyl)-3,5-dichloroquinoxaline수율 129%

시약·촉매·용매 1

HCID 5943Carbon Tetrachloride용매

실험 절차

3,5-Dichloro-2-ethylquinoxaline (1.10 Kg, 4.84 mol) was dissolved in CCl4 (4.4 L) at rt. 1,3-dibromo-5,5-dimethylhydantoin (762 g, 2.66 mol) and benzoyl peroxide (116 g, 0.48 mol) were then added. The resulting suspension was heated at reflux for 2 h. At this time LC-MS analysis showed that the reaction was complete. After cooling to rt white crystals formed in the reaction vessel. The white crystals were collected by filtration, washed with saturated aqueous NaHCO3 (3×5 L), and dried under high vacuum to give 2-(1-bromoethyl)-3,5-dichloroquinoxaline as a white solid (1.05 Kg). 1H NMR (DMSO-d6) δ ppm 8.04-8.12 (m, 2H), 7.78-7.90 (m, 1H), 5.76-5.84 (m, 1H), 2.09 (d, J=6.7 Hz, 3H). Mass Spectrum (ESI) m/z=304.8 [(M+1) (79Br)], 306.9 [(M+1) (81Br)].

후처리

  1. temperatureThe resulting suspension was heated
  2. temperatureat reflux for 2 h
  3. customformed in the reaction vessel
  4. filtrationThe white crystals were collected by filtration
  5. washwashed with saturated aqueous NaHCO3 (3×5 L)
  6. customdried under high vacuum

출처 및 근거

ORD 기록
ord-bddd886454ef4a29a3aa054e356d2cbd
출처 데이터셋
uspto-grants-2014_05
특허 번호
US08716290B2

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