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

HRID 75373Notes

Reaction equation

HRID 75373 reaction equation
[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]

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

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)].

Workup

  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

Sources & evidence

ORD record
ord-e14931c3a7b54cd7b280a4c2b71c8589
Source dataset
uspto-grants-2014_09
Patent number
US08835432B2

Reaction notes

Loading…