Dimethylamine → Acetic acid, (dimethylamino)oxo-, ethyl ester

HRID 875277Notes

Reaction equation

HRID 875277 reaction equation
[CH3:1][NH:2][CH3:3].C[O-].[Na+].[C:7]([O:14]CC)(=O)[C:8]([O:10][CH2:11][CH3:12])=[O:9].P(=O)(O)(O)O>CO>[CH3:1][N:2]([CH3:3])[C:7](=[O:14])[C:8]([O:10][CH2:11][CH3:12])=[O:9]

Participants

6

Reactant 4

HCID 674DimethylamineHCID 1004Phosphoric AcidHCID 7268Diethyl OxalateHCID 10942334Sodium Methoxide

Product 1

HCID 85553Acetic acid, (dimethylamino)oxo-, ethyl ester

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Conditions

Temperature
0 °C

Procedure

In a 1,500 mL reactor, are added at 0° C., 360 g (4 mol) of dimethylamine (DMA) solution at 50% by weight in methanol and 44 g (0.2 mol) of sodium methylate at 25% by weight in methanol. To this mixture are added at 0-5° C. and within 1 hour, 584 g (4 mol) of diethyl oxalate. The mixture is maintained with stirring at 0° C. for 4 hours. The reaction medium is concentrated in vacuo (Pmax=200 mbars) for removing residual DMA and methanol and an 85% orthophosphoric acid solution (23.3 g 0.2 mol) is then added. The salts formed are filtered and the filtrate is then distilled in vacuo (Tbp=77-78° C., P<1 mbar) for recovering the desired product (500 g).

Workup

  1. additionIn a 1,500 mL reactor, are added at 0° C.
  2. additionTo this mixture are added at 0-5° C. and within 1 hour
  3. temperatureThe mixture is maintained
  4. concentrationThe reaction medium is concentrated in vacuo (Pmax=200 mbars)
  5. customfor removing residual DMA and methanol
  6. customThe salts formed
  7. filtrationare filtered
  8. distillationthe filtrate is then distilled in vacuo (Tbp=77-78° C., P<1 mbar)
  9. customfor recovering the desired product (500 g)

Sources & evidence

ORD record
ord-9f57d8313fc0445abbee1c3532e92149
Source dataset
uspto-grants-2015_03
Patent number
US08981148B2

Reaction notes

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