Carbon Tetrachloride → HCID 57708010, compound

HRID 216879Notes

Reaction equation

HRID 216879 reaction equation
[Cl:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[N:4]=[C:5]([CH:19]([CH3:21])[CH3:20])[C:6]([C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([F:18])[CH:13]=1)=[N:7]2.[Cl:22][C:23]1[CH:32]=[CH:31][CH:30]=[C:29]2[C:24]=1[N:25]=[C:26]([C:36]1[CH:41]=[CH:40][CH:39]=[C:38]([F:42])[CH:37]=1)[C:27]([CH:33]([CH3:35])[CH3:34])=[N:28]2.[Br:43]N1C(C)(C)C(=O)N(Br)C1=O.C(Cl)(Cl)(Cl)Cl.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>>[Br:43][C:19]([C:5]1[C:6]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([F:18])[CH:13]=2)=[N:7][C:8]2[C:3]([N:4]=1)=[C:2]([Cl:1])[CH:11]=[CH:10][CH:9]=2)([CH3:21])[CH3:20].[Br:43][C:33]([C:27]1[C:26]([C:36]2[CH:41]=[CH:40][CH:39]=[C:38]([F:42])[CH:37]=2)=[N:25][C:24]2[C:29](=[CH:30][CH:31]=[CH:32][C:23]=2[Cl:22])[N:28]=1)([CH3:35])[CH3:34]

Participants

7

Reactant 5

HCID 5943Carbon TetrachlorideHCID 64791,3-Dibromo-5,5-dimethylhydantoinHCID 7187Benzoyl PeroxideHCID 57707832HCID 57707832, compoundHCID 57707833HCID 57707833, compound

Product 2

HCID 57708010HCID 57708010, compoundHCID 57708058HCID 57708058, compound

Procedure

A mixture of 5-chloro-2-(3-fluorophenyl)-3-isopropylquinoxaline and 5-chloro-3-(3-fluorophenyl)-2-isopropylquinoxaline (3.3042 g, 10.99 mmol) and 1,3-dibromo-5,5-dimethylhydantoin (4.712 g, 16.48 mmol) were suspended in carbon tetrachloride (109.9 mL, 10.99 mmol). To the mixture was added benzoyl peroxide (0.3548 g, 1.099 mmol) and the mixture was heated at reflux. After 20 h, the mixture was cooled to room temperature and concentrated under reduced pressure. The residue was purified by silica gel column chromatography on a 120 g of Redi-Sep™ column using 0 to 10% gradient of EtOAc in hexane over 15 min and then 10% isocratic of EtOAc for 30 min as eluent to give 3-(2-bromopropan-2-yl)-5-chloro-2-(3-fluorophenyl)quinoxaline and 2-(2-bromopropan-2-yl)-5-chloro-3-(3-fluorophenyl)quinoxaline as a yellow solid: LC-MS (ESI) m/z 379.0 and 381.0 [M+H]+. The mixture of two regioisomers was carried as a mixture without further purification for the next step.

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography on a 120 g of Redi-Sep™ column
  5. customover 15 min

Sources & evidence

ORD record
ord-28566c94aa054a27bb05c56f56bbb7f6
Source dataset
uspto-grants-2012_06
Patent number
US08193199B2

Reaction notes

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