Reaction #452253

Reaction equation

water

methyl 2-formylbenzoate

2-amino-2,3-dimethylbutyramide

p-toluenesulfonic acid

→

methyl o-[N-(1-carbamoyl-1,2-dimethylpropyl)formimidoyl]benzoate

Solvents

toluene

Conditions

Workup

1. 1
   Temperatureis heated
2. 2
   FiltrationThe mixture is filtered
3. 3
   Concentrationconcentrated in vacuo
4. 4
   OtherThe residue crystallizes on standing
5. 5
   Otheris recrystallized from etherhexane

Procedure

A mixture containing 5.0 g methyl 2-formylbenzoate [C. Brown and M. V. Sargent, J. Chem. Soc. (C), 1818 (1969)] and 4.0 g 2-amino-2,3-dimethylbutyramide and 50 mg p-toluenesulfonic acid in 100 mL toluene is heated under reflux under a Dean-Stark water separator for three hours. The mixture is filtered and concentrated in vacuo. The residue crystallizes on standing and is recrystallized from etherhexane to give analytically pure methyl o-[N-(1-carbamoyl-1,2-dimethylpropyl)formimidoyl]benzoate, mp 79°-80.5° C.

Source