Water → HCID 69241147, compound

HRID 1907552Notes

Reaction equation

HRID 1907552 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]([Cl:14])[CH:8]=2)[N:3]=1.[CH3:15][O:16][C:17]1[CH:24]=[C:23]([O:25][CH3:26])[CH:22]=[CH:21][C:18]=1[CH2:19][NH2:20].O>CS(C)=O>[Cl:14][C:7]1[CH:8]=[C:9]2[C:4](=[CH:5][CH:6]=1)[N:3]=[C:2]([NH:20][CH2:19][C:18]1[CH:21]=[CH:22][C:23]([O:25][CH3:26])=[CH:24][C:17]=1[O:16][CH3:15])[C:11]([O:12][CH3:13])=[N:10]2

Participants

5

Reactant 3

HCID 962WaterHCID 5972502,4-DimethoxybenzylamineHCID 13385672HCID 13385672, compound

Product 1

HCID 69241147HCID 69241147, compoundYield 78.3%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To 2,6-dichloro-3-methoxyquinoxaline (4.00 g, 17.5 mmol) dissolved in dimethyl-sulfoxide (40 ml), 2,4-dimethoxybenzylamine (14.6 g, 87.3 mmol) was added at room temperature. The mixture was stirred at room temperature for 36 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 (30:1) mixture and concentration gave 4.93 g of the titled compound (yield, 78%).

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 (30:1) mixture and concentration

Sources & evidence

ORD record
ord-d8704d6c43e046df921e6ef5af662b67
Source dataset
uspto-grants-2013_12
Patent number
US08598173B2

Reaction notes

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