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Water → 3,6-Dimethoxy-2-(2,4-dimethoxybenzylamino)quinoxaline

HRID 1907598
Notes
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Reaction equation

HRID 1907598 reaction equation
Cl[C:2]1[C:11]([O:12][CH3:13])=[N:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([O:14][CH3:15])[CH:8]=2)[N:3]=1.[CH3:16][O:17][C:18]1[CH:25]=[C:24]([O:26][CH3:27])[CH:23]=[CH:22][C:19]=1[CH2:20][NH2:21].O>CS(C)=O>[CH3:13][O:12][C:11]1[C:2]([NH:21][CH2:20][C:19]2[CH:22]=[CH:23][C:24]([O:26][CH3:27])=[CH:25][C:18]=2[O:17][CH3:16])=[N:3][C:4]2[C:9]([N:10]=1)=[CH:8][C:7]([O:14][CH3:15])=[CH:6][CH:5]=2
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 962WaterHCID 5972502,4-DimethoxybenzylamineHCID 133856742-Chloro-3,6-dimethoxyquinoxaline

Product 1

HCID 692425723,6-Dimethoxy-2-(2,4-dimethoxybenzylamino)quinoxalineYield 77%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
60 °C

Procedure

To 2-chloro-3,6-dimethoxyquinoxaline (3.87 g, 17.2 mmol) dissolved in dimethyl-sulfoxide (70 ml), 2,4-dimethoxybenzylamine (6.07 g, 36.3 mmol) was added at room temperature. The mixture was stirred at 60° C. for 118 hours and then water was added thereto. The product was extracted with ethyl acetate and the organic layer was washed with water and dried over MgSO4. After concentration under the reduced pressure, the crude product was purified by SiO2 column chromatography. Extraction of the residue with a n-hexane:ethyl acetate (6:1) mixture and concentration gave 4.69 g of the titled compound (yield, 77%).

Workup

  1. extractionThe product was extracted with ethyl acetate
  2. washthe organic layer was washed with water
  3. dry with materialdried over MgSO4
  4. concentrationAfter concentration under the reduced pressure
  5. customthe crude product was purified by SiO2 column chromatography
  6. extractionExtraction of the residue
  7. concentrationwith a n-hexane:ethyl acetate (6:1) mixture and concentration

Sources & evidence

ORD record
ord-931eb2ad454c49d29ad561d08ab259c5
Source dataset
uspto-grants-2013_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08598173B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes