Réaction #9273

Équation de réaction

(2-amino-1,3-benzothiazol-6-yl)methyl cyanide

ethylisocyanate

triethylamine

→

N-(6-Methylcyano-1,3-benzothiazol-2-yl)-N′-ethylurea

Solvants

dimethylformamide

Conditions de réaction

Traitement

1. 1
   Températurethen cooled to RT
2. 2
   AutreThe solvent is removed in vacuo
3. 3
   Lavagethe solids are washed well with ether
4. 4
   AutreThe product is recrystallized from hot EtOAc
5. 5
   AutreLC/MS 2.73 min, 261 (M+1), 259 (M−1)

Mode opératoire

About 1 g of (2-amino-1,3-benzothiazol-6-yl)methyl cyanide is dissolved in about 10 ml dimethylformamide. About 0.8 ml of ethylisocyanate is added followed by about 1.4 ml triethylamine and the solution is heated to about 80° C. under good agitation. The solution is allowed to stir for about 4–6 hours then cooled to RT. The solvent is removed in vacuo and the solids are washed well with ether. The product is recrystallized from hot EtOAc. 1H NMR 1.09 (t, 3H), 3.1 (m, 2H), 4.1 (s, 2H), 6.72 (m, 1H), 7.32 (m, 1H), 7.61 (d, 1H), 7.85 (s, 1H), 10.7 (s, 1H); LC/MS 2.73 min, 261 (M+1), 259 (M−1).

Source