Réaction #955932

Équation de réaction

NaHCO3

2,4-dimethylbenzohydrazide

cyanic bromide

→

5-(2,4-Dimethylphenyl)-1,3,4-oxadiazol-2-amine

Rendement 82.0%

Solvants

water

dioxane

Conditions de réaction

Traitement

1. 1
   ConcentrationThe solution was concentrated
2. 2
   workup.ADDITIONdiluted with water (20 mL)
3. 3
   AutreThe resulting solid was collected
4. 4
   Autredried on vacuum

Mode opératoire

To a solution of 2,4-dimethylbenzohydrazide (example 16b) (2 g) in dry dioxane (12 mL) was added cyanic bromide (1.28 g, 12.2 mmol) followed by a solution of NaHCO3 (1.02 g, 12.2 mmol) in water (12 mL). The resulting mixture was stirred 2 hours at rt. The solution was concentrated to ½ volume on vacuum and diluted with water (20 mL). The resulting solid was collected and dried on vacuum to give 5-(2,4-Dimethylphenyl)-1,3,4-oxadiazol-2-amine (1.88 g, 82%) as a white solid. 1H NMR (300 MHz, dMSO): δ 2.29 (s, 3H), 2.52 (d, 3H), 7.13 (d, 1H), 7.16 (s, 3H), 7.54-7.56 (d, 1H); MS (M+H, 190).

Source