Potassium Carbonate → HCID 22636130, compound

HRID 2415703Notes

Reaction equation

HRID 2415703 reaction equation
[CH3:1][O:2][CH2:3][CH2:4]Br.[CH3:6][N:7]([CH3:34])[C:8]1[CH:9]=[C:10]([NH:14][C:15](=[O:33])[C:16]2[CH:21]=[CH:20][C:19]([CH3:22])=[C:18]([NH:23][C:24](=[O:32])[C:25]3[CH:30]=[CH:29][C:28]([OH:31])=[CH:27][CH:26]=3)[CH:17]=2)[CH:11]=[CH:12][CH:13]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[CH3:34][N:7]([CH3:6])[C:8]1[CH:9]=[C:10]([NH:14][C:15](=[O:33])[C:16]2[CH:21]=[CH:20][C:19]([CH3:22])=[C:18]([NH:23][C:24](=[O:32])[C:25]3[CH:26]=[CH:27][C:28]([O:31][CH2:4][CH2:3][O:2][CH3:1])=[CH:29][CH:30]=3)[CH:17]=2)[CH:11]=[CH:12][CH:13]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 809722-Bromoethyl methyl etherHCID 22636101HCID 22636101, compound

Product 1

HCID 22636130HCID 22636130, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2-Bromoethyl methyl ether (0.033 ml) was added to a stirred suspension of N-(3-dimethylaminophenyl)-3-(4-hydroxybenzamido)4-methylbenzamide (0.9 g) and anhydrous potassium carbonate (0.064 g) in DMF (10 ml) and the resultant mixture was stirred at 80° C. for 5 hours. The mixture was cooled to ambient temperature and partitioned between ethyl acetate and water. The organic phase was washed with a saturated aqueous sodium bicarbonate solution and with a saturated aqueous sodium chloride solution, dried over magnesium sulphate and evaporated. The residue was triturated under diethyl ether. There was thus obtained the title compound as a solid (0.073 g); NMR Spectrum: (DMSOd6) 2.28 (s, 3H), 2.87 (s, 6H), 3.31 (s, 3H), 3.67 (m, 2H), 4.18 (m, 2H), 6.43, (d, 1H) 7.12 (m, 5H), 7.37 (d, 1H), 7.78 (d, 1H), 7.97 (m, 3H), 9.87 (s, 1H), 9.96 (s, 1H); Mass Spectrum: M+H+ 448.

Workup

  1. custompartitioned between ethyl acetate and water
  2. washThe organic phase was washed with a saturated aqueous sodium bicarbonate solution and with a saturated aqueous sodium chloride solution
  3. dry with materialdried over magnesium sulphate
  4. customevaporated
  5. customThe residue was triturated under diethyl ether

Sources & evidence

ORD record
ord-af44d833640b481fbcc343fbd1d8c5a6
Source dataset
uspto-grants-2004_11
Patent number
US06821965B1

Reaction notes

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