Potassium Carbonate → HCID 70234410, compound

HRID 1387453Notes

Reaction equation

HRID 1387453 reaction equation
[CH2:1]([O:3][C:4](=[O:19])[CH:5]=[CH:6][C:7]1[CH:12]=[CH:11][C:10]([NH:13][C:14](=[O:17])[CH2:15]Cl)=[C:9]([OH:18])[CH:8]=1)[CH3:2].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[CH2:1]([O:3][C:4](=[O:19])[CH:5]=[CH:6][C:7]1[CH:12]=[CH:11][C:10]2[NH:13][C:14](=[O:17])[CH2:15][O:18][C:9]=2[CH:8]=1)[CH3:2]

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 541602373-[4-(2-Chloroacetylamino)-3-hydroxyphenyl]acrylic acid ethyl ester

Product 1

HCID 70234410HCID 70234410, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

To a stirred solution of 11-4 (4.28 g, 15.0 mmol) in DMF (50 mL) was added K2CO3 (4.50 g, 32.6 mmol). The resulting suspension was heated to 50° C. for 12 h., after which time the reaction was concentrated. The residue was partitioned between saturated NaHCO3 and EtOAc and extracted twice with EtOAc. The combined organic layers were washed with brine, dried (Na2SO4), and concentrated. Flash chromatography (silica gel; 25:75 EtOAc/hexanes) yielded 11-5 as a beige solid.

Workup

  1. concentrationafter which time the reaction was concentrated
  2. customThe residue was partitioned between saturated NaHCO3 and EtOAc
  3. extractionextracted twice with EtOAc
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-d541471e84094916ac6951f7dbca3320
Source dataset
uspto-grants-2001_07
Patent number
US06268378B1

Reaction notes

Loading…