Diketene → N-(2-Methylpropanoyl)-3-oxobutanamide

HRID 328677Notes

Reaction equation

HRID 328677 reaction equation
[C:1]([NH2:6])(=[O:5])[CH:2]([CH3:4])[CH3:3].[CH2:7]=[C:8]1[O:12][C:10](=[O:11])[CH2:9]1>>[C:10]([NH:6][C:1](=[O:5])[CH:2]([CH3:4])[CH3:3])(=[O:11])[CH2:9][C:8]([CH3:7])=[O:12]

Participants

3

Reactant 2

HCID 12661DiketeneHCID 68424Isobutyramide

Product 1

HCID 12682092N-(2-Methylpropanoyl)-3-oxobutanamideYield 38.7%

Procedure

A 250 ml, three-necked, round bottom flask, was equipped with a condenser, drying tube, mechanical stirrer, gas inlet tube, thermometer and heating mantle. Toluene (100 ml) was introduced and hydrogen chloride gas was bubbled through the solvent until the solution was saturated. Isobutyramide (8.70 g, 0.10 mole) was added and the mixture was heated to 92°. Diketene (8.40 g, 0.10 mole) was added over a 6 minute period and after heating for 15 minutes, a 38.7% yield of N-acetoacetylisobutyramide was obtained.

Workup

  1. customA 250 ml, three-necked, round bottom flask, was equipped with a condenser
  2. customdrying tube, mechanical stirrer, gas inlet tube
  3. temperaturethermometer and heating mantle
  4. additionToluene (100 ml) was introduced
  5. customhydrogen chloride gas was bubbled through the solvent until the solution
  6. temperaturethe mixture was heated to 92°
  7. temperatureafter heating for 15 minutes

Sources & evidence

ORD record
ord-d58c3049331d42269842d30240302ecd
Source dataset
uspto-grants-1977_04
Patent number
US04018771

Reaction notes

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