Cesium carbonate → HCID 69729781, compound

HRID 1062360Notes

Reaction equation

HRID 1062360 reaction equation
Br[CH2:2][C:3]([O:5][CH3:6])=[O:4].C([O-])([O-])=O.[Cs+].[Cs+].[OH:13][C:14]1[CH:15]=[C:16]([NH:20][C:21](=[O:30])[CH:22]=[CH:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH:17]=[CH:18][CH:19]=1>C(#N)C>[CH3:6][O:5][C:3](=[O:4])[CH2:2][O:13][C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([NH:20][C:21](=[O:30])[CH:22]=[CH:23][C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=2)[CH:15]=1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 60984Methyl bromoacetateHCID 721433HCID 721433, compound

Product 1

HCID 69729781HCID 69729781, compoundYield 48.7%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
45 °C

Procedure

A mixture of methyl bromoacetate (0.230 g, 1.93 mmol), Cs2CO3 (0.525 g, 1.60 mmol), and N-(3-hydroxy-phenyl)-3-phenyl-acrylamide (1/91) (0.370 g, 1.55 mmol) in acetonitrile (5 ml) was stirred at 45° C. for 3 hours. The reaction mixture was evaporated and the residue was partitioned between ethyl acetate and 0.1N KHSO4. The organic layer was washed successively with water, brine, and dried (Na2SO4). The solvent was evaporated and the residue was chromatographed silicagel with chloroform-ethyl acetate (10:1) as eluent to give the title compound 8 (0.235 g, 48%). 1H NMR (CDCl3, HMDSO) δ: 3.75 (3H, s); 4.62 (2H, s); 6.53 (1H, d, J=15.6 Hz); 6.68 (1H, t, J=2.0 Hz); 7.01-7.60 (9H, m); 7.71 (1H, d, J=15.6 Hz).

Workup

  1. customThe reaction mixture was evaporated
  2. customthe residue was partitioned between ethyl acetate and 0.1N KHSO4
  3. washThe organic layer was washed successively with water, brine
  4. dry with materialdried (Na2SO4)
  5. customThe solvent was evaporated
  6. customthe residue was chromatographed silicagel with chloroform-ethyl acetate (10:1) as eluent

Sources & evidence

ORD record
ord-23c9b2e5ffd44928b7da9c4e69a3cb86
Source dataset
uspto-grants-2005_11
Patent number
US06960685B2

Reaction notes

Loading…