Sulfuric Acid → HCID 86691798, compound

HRID 875278Notes

Reaction equation

HRID 875278 reaction equation
[CH3:1][N:2]([CH3:9])[C:3](=[O:8])[C:4]([O:6][CH3:7])=[O:5].[CH2:10]([CH:12]([CH2:15][CH2:16][CH2:17][CH3:18])CO)[CH3:11].S(=O)(=O)(O)O>CO>[CH3:1][N:2]([CH3:9])[C:3](=[O:8])[C:4]([O:6][CH2:7][CH:12]([CH2:10][CH3:11])[CH2:15][CH2:16][CH2:17][CH3:18])=[O:5]

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 77202-EthylhexanolHCID 13280608Methyl (dimethylamino)(oxo)acetate2×

Product 1

HCID 86691798HCID 86691798, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
80 °C

Procedure

In a 1,000 mL reactor, are mixed at 20-25° C., methyl 2-(dimethylamino)-2-oxoacetate (compound 1) (390 g, 2.98 mol), 2-ethyl-hexan-1-ol (464 g, 3.5 mol) and 98% sulfuric acid (66 g, 0.67 mol). The temperature of the mixture is brought to and maintained at 80° C. for 24 hours. The progression of the reaction is tracked by gas chromatography analysis. At the end of the reaction, the methanol formed is removed from the reaction medium by distillation under reduced vacuum (Pmin=150 mbars) and an aqueous solution of sodium hydrogencarbonate is then added to the reaction medium so that the final pH is 7. The organic phase is separated from the aqueous phase. The latter is counter-extracted with 500 mL of dichloromethane. The organic phases are collected and then the reaction medium is concentrated in order to remove the dichloromethane. To the residue, are added 5 g of potassium carbonate and the thereby obtained medium is then distilled under partial vacuum (Tbp 150° C., P<1 mbar). The expected product is obtained with a purity of more than 98% (578 g).

Workup

  1. additionIn a 1,000 mL reactor, are mixed at 20-25° C.
  2. customAt the end of the reaction
  3. customis removed from the reaction medium by distillation under reduced vacuum (Pmin=150 mbars)
  4. additionan aqueous solution of sodium hydrogencarbonate is then added to the reaction medium so that the final pH is 7
  5. customThe organic phase is separated from the aqueous phase
  6. extractionThe latter is counter-extracted with 500 mL of dichloromethane
  7. customThe organic phases are collected
  8. concentrationthe reaction medium is concentrated in order
  9. customto remove the dichloromethane
  10. additionTo the residue, are added 5 g of potassium carbonate
  11. customthe thereby obtained medium
  12. distillationis then distilled under partial vacuum (Tbp 150° C., P<1 mbar)

Sources & evidence

ORD record
ord-dc6c20b60a76442cb4b3254c438dfdf0
Source dataset
uspto-grants-2015_03
Patent number
US08981148B2

Reaction notes

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