Sodium Bicarbonate → ethyl 4-[2-(N-ethoxycarbonyl-N-methylaminomethyl)morpholino]-2,3,5-trifluorobenzoate

HRID 477829Notes

Reaction equation

HRID 477829 reaction equation
[F:1][C:2]1[C:12]([F:13])=[C:11](F)[C:10]([F:15])=[CH:9][C:3]=1[C:4]([O:6][CH2:7][CH3:8])=[O:5].[CH2:16]([O:18][C:19]([N:21]([CH2:23][CH:24]1[O:29][CH2:28][CH2:27][NH:26][CH2:25]1)[CH3:22])=[O:20])[CH3:17].C(=O)([O-])O.[Na+]>C(#N)C>[CH2:16]([O:18][C:19]([N:21]([CH2:23][CH:24]1[CH2:25][N:26]([C:11]2[C:10]([F:15])=[CH:9][C:3]([C:4]([O:6][CH2:7][CH3:8])=[O:5])=[C:2]([F:1])[C:12]=2[F:13])[CH2:27][CH2:28][O:29]1)[CH3:22])=[O:20])[CH3:17]

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 2774395Ethyl 2H-tetrafluorobenzoateHCID 146525772-(N-ethoxycarbonyl-N-methylaminomethyl)morpholine

Product 1

HCID 14652578ethyl 4-[2-(N-ethoxycarbonyl-N-methylaminomethyl)morpholino]-2,3,5-trifluorobenzoateYield 72%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A suspension of 22.2 g of ethyl 2,3,4,5-tetrafluorobenzoate, 22.2 g of 2-(N-ethoxycarbonyl-N-methylaminomethyl)morpholine and 8.4 g of sodium hydrogen carbonate in 130 ml of acetonitrile is refluxed for 7 hours. The reaction mixture is concentrated under reduced pressure, to the obtained residue is added 100 ml of chloroform and the solution is washed with water. After drying over anhydrous magnesium sulfate, the chloroform is distilled off under reduced pressure and the residue is puiified by chromatography on silica gel to give 29.0 g of ethyl 4-[2-(N-ethoxycarbonyl-N-methylaminomethyl)morpholino]-2,3,5-trifluorobenzoate in 72% yield, as an oily substance.

Workup

  1. temperatureis refluxed for 7 hours
  2. concentrationThe reaction mixture is concentrated under reduced pressure, to the obtained residue
  3. additionis added 100 ml of chloroform
  4. washthe solution is washed with water
  5. dry with materialAfter drying over anhydrous magnesium sulfate
  6. distillationthe chloroform is distilled off under reduced pressure

Sources & evidence

ORD record
ord-ecf351690b264876a0a5066aae92a573
Source dataset
uspto-grants-1989_12
Patent number
US04889857

Reaction notes

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