Sulfuric Acid → trimethylpyruvic acid N-acetylamide

HRID 1447056Notes

Reaction equation

HRID 1447056 reaction equation
[C:1](OC(=O)C)(=[O:3])[CH3:2].[C:8]([C:14]#[N:15])(=[O:13])[C:9]([CH3:12])([CH3:11])[CH3:10].S(=O)(=O)(O)[OH:17]>>[C:1]([NH:15][C:14](=[O:17])[C:8]([C:9]([CH3:12])([CH3:11])[CH3:10])=[O:13])(=[O:3])[CH3:2]

Participants

4

Reactant 3

HCID 1118Sulfuric AcidHCID 7918Acetic AnhydrideHCID 945273,3-Dimethyl-2-oxobutanenitrile

Product 1

HCID 12769196trimethylpyruvic acid N-acetylamideYield 86.5%

Procedure

First 25.6 g (0.25 mol) of acetic anhydride and then 27.8 g (0.25 mol) of pivaloyl cyanide were introduced, in each case at room temperature, into 49.0 g (0.5 mol) of concentrated sulphuric acid, which had been initially introduced into the reaction vessel. After subsequently stirring the reaction mixture for 4 hours, 150 g of icewater were added and the mixture was stirred thoroughly. The reaction product which precipitated was filtered off, washed with 100 ml of water and dried. 37.0 g (86.5% of theory) of trimethylpyruvic acid N-acetylamide were obtained as colorless glistening flakes of melting point 82°-84° C.; content, according to determination by gas chromatography, >98%. No additional purification operations were required for further reactions.

Workup

  1. additionhad been initially introduced into the reaction vessel
  2. addition150 g of icewater were added
  3. stirringthe mixture was stirred thoroughly
  4. customThe reaction product which precipitated
  5. filtrationwas filtered off
  6. washwashed with 100 ml of water
  7. customdried

Sources & evidence

ORD record
ord-fdff00a62a614d81b6ae35b251b39a0c
Source dataset
uspto-grants-1982_02
Patent number
US04315094

Reaction notes

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