Potassium Carbonate → HCID 67974987, compound

HRID 2174465Notes

Reaction equation

HRID 2174465 reaction equation
[Cl:1][C:2]1[CH:8]=[CH:7][C:6]([O:9][CH2:10][CH2:11][N:12]2[CH2:17][CH2:16][O:15][CH2:14][CH2:13]2)=[CH:5][C:3]=1[NH2:4].C([O-])([O-])=O.[K+].[K+].[C:24](Cl)(=[O:33])[CH:25]=[CH:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1>CC(C)=O.O>[Cl:1][C:2]1[CH:8]=[CH:7][C:6]([O:9][CH2:10][CH2:11][N:12]2[CH2:17][CH2:16][O:15][CH2:14][CH2:13]2)=[CH:5][C:3]=1[NH:4][C:24](=[O:33])[CH:25]=[CH:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 660233-Phenylprop-2-enoyl chlorideHCID 39358843HCID 39358843, compound

Product 1

HCID 67974987HCID 67974987, compoundYield 60%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Procedure

2-chloro-5-(2-morpholinoethoxy)aniline (1.9 g, 7.4 mmol, 1 eq.) was placed in a mixture of acetone (2.5 mL) and water (3.2 mL) in the presence of K2CO3 (2.1 g, 14.4 mmol, 2 eq.). Cinnamoyl chloride (1.2 g, 7.4 mmol, 1 eq.) was then added at 0° C. The reaction mixture was allowed to warm-up to room temperature, stirred for 2 hours and extracted with ethyl acetate. The organic phase was dried over MgSO4, filtered and concentrated under reduced pressure. The resulting residue was purified by column chromatography on silica gel to afford N-(2-chloro-5-(2-morpholinoethoxy)phenyl)cinnamamide (1.7 g, 60%).

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe organic phase was dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe resulting residue was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-3ae178e565aa4865af37a6b93a96fbf5
Source dataset
uspto-grants-2015_06
Patent number
US09061999B2

Reaction notes

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