Reaction #4224

ord-aa9ed74e9a0d49428bacce5162b0c162

Reaction equation

CC1=C(C)C(=O)OC1=O
dimethylmaleic acid anhydride
CC(C)C(C)(N)C(N)=O
2-amino-2,3-dimethylbutyric acid amide
→
C/C(C(=O)O)=C(\C)C(=O)NC(C)(C(N)=O)C(C)C
desired compound ( II )
Yield 96.3%
C/C(C(=O)O)=C(\C)C(=O)NC(C)(C(N)=O)C(C)C
2,3-Dimethyl-N-(1-aminocarbonyl-1,2-dimethyl-propyl)maleic acid monoamide
Yield 96.3%

Reactants

CC1=C(C)C(=O)OC1=O
dimethylmaleic acid anhydride
CC(C)C(C)(N)C(N)=O
2-amino-2,3-dimethylbutyric acid amide

Reagents

None

Solvents

ClCCl
methylene chloride

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    Temperaturewas heated at its boiling point for 15 minutes
  2. 2
    workup.DISTILLATIONAfter some of the solvent had been distilled off
  3. 3
    Otherthe product precipitated
  4. 4
    Filtrationthereby was suction-filtered off

Procedure

A mixture of 46 g of dimethylmaleic acid anhydride, 48 g of 2-amino-2,3-dimethylbutyric acid amide and 70 ml of methylene chloride was heated at its boiling point for 15 minutes. After some of the solvent had been distilled off, the residual mixture was stirred with 300 ml of diethyl ether, and the product precipitated thereby was suction-filtered off. The desired compound (II) (90 g; 96%) was isolated as a crystalline solid, melting point 70°-72° C.

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US04723989uspto-grants-1988_02