Potassium Carbonate → HCID 54061983, compound

HRID 1530933Notes

Reaction equation

HRID 1530933 reaction equation
[CH2:1]([O:3][C:4](=[O:20])[CH2:5][N:6]=[C:7]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[CH3:2].C([C:28]1[CH:36]=[C:35]([CH2:37]Br)[CH:34]=[CH:33][C:29]=1[C:30]([OH:32])=[O:31])C1C=CC=CC=1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[CH2:1]([O:3][C:4](=[O:20])[C@H:5]([CH2:37][C:35]1[CH:36]=[CH:28][C:29]([C:30]([O:32][CH2:7][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[O:31])=[CH:33][CH:34]=1)[N:6]=[C:7]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1)[CH3:2]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 319508Ethyl 2-(diphenylmethyleneamino)acetateHCID 21253314HCID 21253314, compound

Product 1

HCID 54061983HCID 54061983, compoundYield 212.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of N-(diphenylmethylene)glycine ethyl ester (6.6 g, 24.9 mmol), benzyl 4-(bromomethyl)benzoic acid (7.61 g, 24.9 mmol) and potassium carbonate (50 mmol, 6.9 g) in acetonitrile (300 ml) was refluxed overnight. The solvent was removed in vacuo and the residue partitioned between EtOAc and water. The aqueous layer was extracted with EtOAc and the combined organic extracts were dried (Na2SO4) and concentrated in vacuo to give the title compound as an oil (13.0 g) δH (CDCl3) 7.90 (2 H, d, J 8.3 Hz), 7.58 (2 H, d, J 7.3 Hz), 7.50-7.25 (11 H, m), 7.14 (2 H, d, J 8.1 Hz), 6.65 (2 H, d, J 6.8 Hz), 5.33 (2 H, m), 4.30-4.15 (3 H, br m), 3.32 (2 H, v br s) and 1.26 (3 H, t, J 7.1 Hz); m/z (ESI, 60 V) 492 (MH+).

Workup

  1. temperaturewas refluxed overnight
  2. customThe solvent was removed in vacuo
  3. customthe residue partitioned between EtOAc and water
  4. extractionThe aqueous layer was extracted with EtOAc
  5. dry with materialthe combined organic extracts were dried (Na2SO4)
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-c98b9827850b481f8d7bc264d500c8aa
Source dataset
uspto-grants-2001_03
Patent number
US06197794B1

Reaction notes

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