Sulfuric Acid → HCID 68235800, compound

HRID 875279Notes

Reaction equation

HRID 875279 reaction equation
[CH3:1][N:2]([CH3:9])[C:3](=[O:8])[C:4]([O:6][CH3:7])=[O:5].[CH:10]1(O)[CH2:15][CH2:14]C[CH2:12][CH2:11]1.S(=O)(=O)(O)O>CO>[CH3:1][N:2]([CH3:9])[C:3](=[O:8])[C:4]([O:6][CH:7]1[CH2:14][CH2:15][CH2:10][CH2:11][CH2:12]1)=[O:5]

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 7966CyclohexanolHCID 13280608Methyl (dimethylamino)(oxo)acetate2×

Product 1

HCID 68235800HCID 68235800, 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) (393 g, 3 mol), cyclohexanol (360 g, 3.6 mol) and 98% sulfuric acid (66 g, 0.67 mol). The temperature of the mixture is brought to and maintained at 80° C. for 36 hours. Progression of the reaction is followed by gas chromatography analysis. At the end of the reaction, the methanol formed is removed from the reaction medium by distillation under reduced vacuum (P min=150 mbars) and an aqueous solution of sodium hydrogen carbonate 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 the reaction medium is then concentrated for removing the dichloromethane. To the residue are added 5 g of potassium carbonate and the thereby obtained medium is then distilled under partial vacuum (Tbp 115-120° C., P<1 mbar). The expected product is obtained with a purity of more than 98.2% (466 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 (P min=150 mbars)
  4. additionan aqueous solution of sodium hydrogen carbonate 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 then concentrated
  9. customfor removing 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 115-120° C., P<1 mbar)

Sources & evidence

ORD record
ord-9b23f7e45f07494cb8455daee6b7730b
Source dataset
uspto-grants-2015_03
Patent number
US08981148B2

Reaction notes

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