Dimethylformamide → HCID 86630635, compound

HRID 2044914Notes

Reaction equation

HRID 2044914 reaction equation
BrCC1C(C2C=CC=CC=2Cl)=NC2C(N=1)=C(Cl)C=CC=2.Br[CH2:22][C:23]1[C:32]([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][C:34]=2[Cl:39])=[N:31][C:30]2[C:25](=[CH:26][CH:27]=[CH:28][C:29]=2[Cl:40])[N:24]=1.CN(C=O)C.[N-:46]=[N+:47]=[N-:48].[Na+]>>[N:46]([CH2:22][C:23]1[C:32]([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][C:34]=2[Cl:39])=[N:31][C:30]2[C:25](=[CH:26][CH:27]=[CH:28][C:29]=2[Cl:40])[N:24]=1)=[N+:47]=[N-:48]

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 33557Sodium AzideHCID 57556154HCID 57556154, compoundHCID 57556186HCID 57556186, compound

Product 1

HCID 86630635HCID 86630635, compound

Procedure

To a stirring solution of a mixture of 3-(bromomethyl)-5-chloro-2-(2-chlorophenyl)quinoxaline and 2-(bromomethyl)-5-chloro-3-(2-chlorophenyl)-quinoxaline (8.5418 g, 23.21 mmol) in DMF (100.0 mL, 23.21 mmol) was added sodium azide (3.017 g, 46.42 mmol) at room temperature and the mixture was stirred at room temperature. After 40 min, the mixture was partitioned between EtOAc (200 mL) and H2O (100 mL). The organic layer was washed with brine (100 mL×1), dried over Na2SO4, filtered, and concentrated under reduced pressure to give 2-(azidomethyl)-5-chloro-3-(2-chlorophenyl)quinoxaline as a brown liquid: LC-MS (ESI) major peak of m/z 330.1 [M+H]+. The crude product was carried on crude without purification for the next step.

Workup

  1. customthe mixture was partitioned between EtOAc (200 mL) and H2O (100 mL)
  2. washThe organic layer was washed with brine (100 mL×1)
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-6e083d20f1b5400eba9bc44594a3d4d8
Source dataset
uspto-grants-2013_11
Patent number
US08586739B2

Reaction notes

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