Acetic Acid → Trimethylpyruvic acid amide

HRID 1105653Notes

Reaction equation

HRID 1105653 reaction equation
Cl.C(O)(=[O:4])C.[C:6]([C:12]#[N:13])(=[O:11])[C:7]([CH3:10])([CH3:9])[CH3:8].C(=O)(O)[O-].[Na+]>>[CH3:8][C:7]([CH3:10])([CH3:9])[C:6](=[O:11])[C:12]([NH2:13])=[O:4]

Participants

5

Reactant 4

HCID 176Acetic AcidHCID 313Hydrochloric AcidHCID 945273,3-Dimethyl-2-oxobutanenitrileHCID 516892Sodium Bicarbonate

Product 1

HCID 12922742Trimethylpyruvic acid amideYield 75.2%

Procedure

Hydrogen chloride was passed into a mixture of 60 g (1 mole) of glacial acetic acid and 111.0 g (1 mole) of pivaloyl cyanide at 20° to 25° C. and under 8 bars for 5 hours. The reaction mixture was then let down and poured onto an excess of a saturated sodium bicarbonate solution. The mixture was extracted three times with 200 ml of methylene chloride each time. The combined organic phases were washed with 200 ml of water, dried over sodium sulphate and concentrated by distilling off the solvent in vacuo. The residue which remained crystallized after a short time. Recrystallization from petroleum ether gave 97 g (75.2% of theory) of trimethylpyruvic acid amide of melting point 68° to 69° C.

Workup

  1. extractionThe mixture was extracted three times with 200 ml of methylene chloride each time
  2. washThe combined organic phases were washed with 200 ml of water
  3. dry with materialdried over sodium sulphate
  4. concentrationconcentrated
  5. distillationby distilling off the solvent in vacuo
  6. customThe residue which remained crystallized after a short time
  7. customRecrystallization from petroleum ether

Sources & evidence

ORD record
ord-fc3cb01216d4409db82476a1b6ea50c4
Source dataset
uspto-grants-1982_01
Patent number
US04309538

Reaction notes

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