Reaktion #444482

Reaktionsgleichung

methyl 2-methyl-4-isopropyl-5-methylsulfonylbenzoate

guanidine

isopropylzinc chloride

methyl 2-methyl-4-bromo-5-methylsulfonylbenzoate

→

N-diaminomethylene-2-methyl-4-isopropyl-5-methylsulfonylbenzamide

Lösungsmittel

methanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigethe solvent is then removed
2. 2
   workup.ADDITIONThe residue is treated with water
3. 3
   Filtrationthe remaining crystalline crop is filtered off with suction
4. 4
   workup.ADDITIONtreated with dil. sodium hydroxide solution
5. 5
   FiltrationThe solid residue is filtered off
6. 6
   Sonstigerecrystallized from ethanol

Vorschrift

A solution of 1.4 g of methyl 2-methyl-4-isopropyl-5-methylsulfonylbenzoate [obtainable by reacting methyl 2-methyl-4-bromo-5-methylsulfonylbenzoate with isopropylzinc chloride in the presence of Pd(II) 1,1'-bis(diphenylphosphine)ferrocene chloride and CuI] and 1.5 g of guanidine in 50 ml of methanol is boiled for five hours and the solvent is then removed. The residue is treated with water and the remaining crystalline crop is filtered off with suction and treated with dil. sodium hydroxide solution. The solid residue is filtered off and recrystallized from ethanol, and N-diaminomethylene-2-methyl-4-isopropyl-5-methylsulfonylbenzamide is obtained, m.p. 220°-223°.

Quelle