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

HRID 903492

Reaction equation

HRID 903492 reaction equation
[C:1]([C:7]#[N:8])(=[O:6])[C:2]([CH3:5])([CH3:4])[CH3:3].S(=O)(=O)(O)[OH:10].[CH3:14][C:15](=[CH2:17])[CH3:16]>C(O)(=O)C>[C:15]([NH:8][C:7](=[O:10])[C:1]([C:2]([CH3:5])([CH3:4])[CH3:3])=[O:6])([CH3:16])([CH3:14])[CH3:17]

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 8255IsobutyleneHCID 945273,3-Dimethyl-2-oxobutanenitrile

Product 1

HCID 13355144N-tert-Butyl-3,3-dimethyl-2-oxobutanamideYield 87%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

There were present in a stirrer apparatus protected against moisture 111 grams (1.0 mole) of pivaloyl cyanide, 150 grams (1.5 moles) of concentrated sulfuric acid and 150 ml of glacial acetic acid and there were led in during one hour under stirring at 0°-5° C. 112 grams (2.0 moles) of isobutylene. Then the mixture was warmed up to room temperature and stirred further for 4 hours. Then the mixture was poured on 500 grams of ice and after thorough stirring the precipitated amide was filtered off with suction. After the drying in the vacuum drying cabinet, there were isolated 161 grams of analytically pure trimethyl pyruvic acid-N-t-butylamide which corresponds to a yield of 87% based on the acyl cyanide employed. The amide has a melting point of 65° C.

Workup

  1. customThere were present in a stirrer
  2. customwere led in during one hour
  3. stirringstirred further for 4 hours
  4. filtrationwas filtered off with suction
  5. customAfter the drying in the vacuum drying cabinet

Sources & evidence

ORD record
ord-526759c3730048e3a8ddb69b99076198
Source dataset
uspto-grants-1980_10
Patent number
US04228082

Linked notes

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