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

HRID 1019809ノート

反応式

HRID 1019809 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 5943Carbon Tetrachloride溶媒

実験手順

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)].

後処理

  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

出典と根拠

ORDレコード
ord-bddd886454ef4a29a3aa054e356d2cbd
出典データセット
uspto-grants-2014_05
特許番号
US08716290B2

反応ノート

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