Diethyl Ether → HCID 66819608, compound

HRID 880822Notes

Reaction equation

HRID 880822 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:9](=O)[CH2:10][O:11][C:12]2[CH:20]=[CH:19][CH:18]=[CH:17][C:13]=2[C:14]([NH2:16])=[O:15])[CH:6]=[CH:7][CH:8]=1.C1(C)C=CC(S(O)(=O)=O)=CC=1.C(OCC)(=O)C.C(OCC)C>C1(C)C=CC=CC=1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:9]2[NH:16][C:14](=[O:15])[C:13]3[CH:17]=[CH:18][CH:19]=[CH:20][C:12]=3[O:11][CH:10]=2)[CH:6]=[CH:7][CH:8]=1

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 6101p-Toluenesulfonic acidHCID 8857Ethyl AcetateHCID 43612366HCID 43612366, compound

Product 1

HCID 66819608HCID 66819608, compoundYield 89.7%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A well stirred suspension of 9 g (31.5 mmol) of 2-[2-(3-Methoxy-phenyl)-2-oxo-ethoxy]-benzamide and 0.3 g (1.58 mmol) of p-toluenesulphonic acid in toluene (0.3 L) was refluxed with a Dean-Stark apparatus for 2 hours. After concentration of the solvent under reduced pressure, the residue was treated with ethyl acetate and diethyl ether and the resulting solid was filtered, washed with a mixture of the aforementioned solvents, dried in vacuo, affording 7.55 g of the title compound (83%).

Workup

  1. temperaturewas refluxed with a Dean-Stark apparatus for 2 hours
  2. filtrationthe resulting solid was filtered
  3. washwashed with a mixture of the aforementioned solvents
  4. customdried in vacuo

Sources & evidence

ORD record
ord-e3918527ce774079bd39e91e0724040e
Source dataset
uspto-grants-2015_03
Patent number
US08993594B2

Reaction notes

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