Potassium Carbonate → Benzyl 5-(4,6-Dimethoxy-1,3,5-triazin-2-yl)oxy-2-methyl-3-methoxycarbonylbenzofuran-4-carboxylate

HRID 52001Notes

Reaction equation

HRID 52001 reaction equation
[OH:1][C:2]1[C:15]([C:16]([O:18][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[O:17])=[C:6]2[C:7]([C:11]([O:13][CH3:14])=[O:12])=[C:8]([CH3:10])[O:9][C:5]2=[CH:4][CH:3]=1.[CH3:26][O:27][C:28]1[N:33]=[C:32]([O:34][CH3:35])[N:31]=[C:30](S(C)(=O)=O)[N:29]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[CH3:35][O:34][C:32]1[N:33]=[C:28]([O:27][CH3:26])[N:29]=[C:30]([O:1][C:2]2[C:15]([C:16]([O:18][CH2:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)=[O:17])=[C:6]3[C:7]([C:11]([O:13][CH3:14])=[O:12])=[C:8]([CH3:10])[O:9][C:5]3=[CH:4][CH:3]=2)[N:31]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 157900444,6-Dimethoxy-2-methylsulfonyl-1,3,5-triazineHCID 54269833Benzyl 5-hydroxy-2-methyl-3-methoxycarbonylbenzofuran-4-carboxylate

Product 1

HCID 54466231Benzyl 5-(4,6-Dimethoxy-1,3,5-triazin-2-yl)oxy-2-methyl-3-methoxycarbonylbenzofuran-4-carboxylateYield 109.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

A mixture comprising 2 g of benzyl 5-hydroxy-2-methyl-3-methoxycarbonylbenzofuran-4-carboxylate, 1 g of 4,6-dimethoxy-2-methylsulfonyl-1,3,5-triazine and 1 g of potassium carbonate in 20 ml of N,N-dimethylformamide, was heated and stirred at 70° C. for two hours. The mixture was returned to room temperature, poured into ice water and extracted with ethyl acetate. The organic layer was washed with water and then dried over anhydrous sodium sulfate. Then, it was concentrated under reduced pressure, and the obtained solid was thoroughly washed with ethanol to obtain 2.4 g (yield: 86%) of the desired compound.

Workup

  1. temperaturewas heated
  2. customwas returned to room temperature
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with water
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationThen, it was concentrated under reduced pressure
  7. washthe obtained solid was thoroughly washed with ethanol

Sources & evidence

ORD record
ord-c8aeca6db46d47d69486361733e264f1
Source dataset
uspto-grants-1997_04
Patent number
US05616537

Reaction notes

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