Sulfuric Acid → 2-Cyano-3-methylbutanoic acid

Reaction equation

C(C(C(C)C)C(NC(N)=O)=O)#N.C(CC(OC)=O)#N.[C:20]([CH:22]([CH:27]([CH3:29])[CH3:28])[C:23]([O:25]C)=[O:24])#[N:21].[OH-].[Na+].S(=O)(=O)(O)O>CC(C)=O>[C:20]([CH:22]([CH:27]([CH3:29])[CH3:28])[C:23]([OH:25])=[O:24])#[N:21]

Participants

Reactant 5

HCID 1118Sulfuric Acid

HCID 7747Methyl cyanoacetate

HCID 14798Sodium Hydroxide

HCID 557651Methyl 2-cyano-3-methylbutanoate

HCID 9793952N-(2-cyano-3-methylbutanoyl)urea

Product 1

HCID 2553382-Cyano-3-methylbutanoic acid

Reagents, catalysts & solvents 1

Procedure

The starting compound, N-(2-cyano-3-methylbutanoyl)urea, is a known compound and can be obtained by, for example, reacting methyl cyanoacetate and acetone, hydrolyzing the resulting methyl 2-cyano-3-methylbutyrate with an aqueous sodium hydroxide solution, treating said reaction mixture with sulfuric acid to give 2-cyano-3-methylbutyric acid and heating this compound in the presence of urea and acetic anhydride.