Sulfuric Acid → N-tert-Butyl-3,3-dimethyl-2-oxobutanamide

HRID 67198

Reaction equation

HRID 67198 reaction equation
[C:1]([C:7]#[N:8])(=[O:6])[C:2]([CH3:5])([CH3:4])[CH3:3].CO[C:11]([CH3:14])([CH3:13])[CH3:12].S(=O)(=O)(O)[OH:16]>C(O)(=O)C>[C:11]([NH:8][C:7](=[O:16])[C:1]([C:2]([CH3:5])([CH3:4])[CH3:3])=[O:6])([CH3:14])([CH3:13])[CH3:12]

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 15413tert-Butyl methyl etherHCID 945273,3-Dimethyl-2-oxobutanenitrile

Product 1

HCID 13355144N-tert-Butyl-3,3-dimethyl-2-oxobutanamide

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

27.8 (0.25 mole) of pivaloyl cyanide, dissolved in 22 g (0.25 mole) of t-butyl methyl ether were added to a reaction mixture, which had been initially introduced into the reaction vessel, consisting of 37.5 g of concentrated sulphuric acid and 52.5 g of glacial acetic acid at 20° to 30° C. in the course of 30 minutes. After subsequently stirring the reaction mixture at room temperature for 2 hours, it was poured onto 125 g of ice and stirred thoroughly. The product which precipitated was filtered off, washed with water and dried. 40.8 g (87.5% of theory) of analytically pure trimethylpyruvic acid N-tert.-butylamide with a melting point of 65° C. and a content of >99% (determined by gas chromatography) were obtained.

Workup

  1. additionwere added to a reaction mixture, which
  2. additionhad been initially introduced into the reaction vessel
  3. stirringstirred thoroughly
  4. customThe product which precipitated
  5. filtrationwas filtered off
  6. washwashed with water
  7. customdried

Sources & evidence

ORD record
ord-89f5f9d49d7f41f38de44e6c05b4f2eb
Source dataset
uspto-grants-1982_08
Patent number
US04345100

Linked notes

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