Dimethylamine → Methyl (dimethylamino)(oxo)acetate

HRID 1527807Notes

Reaction equation

HRID 1527807 reaction equation
[CH3:1][NH:2][CH3:3].C[O-].[Na+].[C:7]([O:13]C)(=O)[C:8]([O:10][CH3:11])=[O:9].P(=O)(O)(O)O>CO>[CH3:1][N:2]([CH3:3])[C:7](=[O:13])[C:8]([O:10][CH3:11])=[O:9]

Participants

6

Reactant 4

HCID 674DimethylamineHCID 1004Phosphoric AcidHCID 11120Dimethyl oxalateHCID 10942334Sodium Methoxide

Product 1

HCID 13280608Methyl (dimethylamino)(oxo)acetate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Conditions

Temperature
0 °C

Procedure

In a 1,000 mL reactor are added at 0° C., 360 g (4 mol) of dimethylamine (DMA) solution at 50% by weight in methanol and 43.2 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, 472 g (4 mol) of dimethyl oxalate. The mixture is maintained with stirring and at 0° C. for 2 hours. The reaction medium is concentrated in vacuo (Pmax=200 mbar) for removing residual DMA and methanol and an 85% orthophosphoric acid solution (23 g 0.2 mol) is then added. The salts formed are filtered and then the filtrate is distilled in vacuo (Tbp=68-70° C., P<1 mbar) in order to recover the desired product (461 g).

Workup

  1. additionIn a 1,000 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 mbar)
  5. customfor removing residual DMA and methanol
  6. customThe salts formed
  7. filtrationare filtered
  8. distillationthe filtrate is distilled in vacuo (Tbp=68-70° C., P<1 mbar) in order
  9. customto recover the desired product (461 g)

Sources & evidence

ORD record
ord-3a317ac43bf74c7da637f562c2eca6f9
Source dataset
uspto-grants-2015_07
Patent number
US09090538B2

Reaction notes

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