Dimethylmaleic anhydride → 2,3-Dimethyl-N-(1-aminocarbonyl-1,2-dimethyl-propyl)maleic acid monoamide

HRID 4128

Reaction equation

HRID 4128 reaction equation
[CH3:1][C:2]1=[C:3]([CH3:9])[C:4]([O:6][C:7]1=[O:8])=[O:5].[NH2:10][C:11]([CH3:18])([CH:15]([CH3:17])[CH3:16])[C:12]([NH2:14])=[O:13]>C(Cl)Cl>[CH3:9]/[C:3](=[C:2](\[CH3:1])/[C:7]([OH:6])=[O:8])/[C:4]([NH:10][C:11]([C:12]([NH2:14])=[O:13])([CH3:18])[CH:15]([CH3:17])[CH3:16])=[O:5]

Participants

4

Reactant 2

HCID 13010Dimethylmaleic anhydrideHCID 97937732-Amino-2,3-dimethylbutanamide

Product 1

HCID 138831692,3-Dimethyl-N-(1-aminocarbonyl-1,2-dimethyl-propyl)maleic acid monoamideYield 96.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

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.

Workup

  1. temperaturewas heated at its boiling point for 15 minutes
  2. distillationAfter some of the solvent had been distilled off
  3. customthe product precipitated
  4. filtrationthereby was suction-filtered off

Sources & evidence

ORD record
ord-aa9ed74e9a0d49428bacce5162b0c162
Source dataset
uspto-grants-1988_02
Patent number
US04723989

Linked notes

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