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

HRID 1878252Notes

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

Participants

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

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

Sources & evidence

ORD record: ord-ac907c41e9d8481daeefab06bb1ca0af
Source dataset: uspto-grants-2012_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08314100B2

Reaction notes

Loading…