Water → (6-Bromo-quinoxalin-2-yl)-(3-chloro-benzyl)-amine

HRID 1020734Notes

Reaction equation

HRID 1020734 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7](Cl)[CH:6]=[N:5]2.[Cl:13][C:14]1[CH:15]=[C:16]([CH:19]=[CH:20][CH:21]=1)[CH2:17][NH2:18].O>CS(C)=O>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([NH:18][CH2:17][C:16]1[CH:19]=[CH:20][CH:21]=[C:14]([Cl:13])[CH:15]=1)[CH:6]=[N:5]2

Participants

5

Reactant 3

HCID 962WaterHCID 77802Benzenemethanamine, 3-chloro-HCID 126864086-Bromo-2-chloroquinoxaline

Product 1

HCID 66797253(6-Bromo-quinoxalin-2-yl)-(3-chloro-benzyl)-amine

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a solution of 6-Bromo-2-chloro-quinoxaline (0.3 g, 1 eq., 1.23 mmol) in DMSO (9 mL), was added 3-chloro benzyl amine (0.87 g, 5 eq., 6.2 mmol) at room temperature. The reaction mixture was stirred at room temperature overnight. After completion of the reaction, water (60 mL) was added and the reaction mixture was extracted with ethyl acetate (30 mL×3). The organic layer was washed with water (60 mL) and brine (60 mL), then dried over Na2SO4. The organic layer was concentrated under vacuum to obtain the crude product.

Workup

  1. additionwas added
  2. extractionthe reaction mixture was extracted with ethyl acetate (30 mL×3)
  3. washThe organic layer was washed with water (60 mL) and brine (60 mL)
  4. dry with materialdried over Na2SO4
  5. concentrationThe organic layer was concentrated under vacuum

Sources & evidence

ORD record
ord-cbc5967b404645719c641b283b111c80
Source dataset
uspto-grants-2014_05
Patent number
US08716473B2

Reaction notes

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