Reaction #169894

Reaction equation

N-{4-[4-(3-chlorophenyl)-5-oxo-4,5-dihydro-1,2,4-oxadiazol-3-yl]-1,2,5-oxadiazol-3-yl}-N′-phenylurea

sodium hydroxide

→

desired product

4-[Bis(anilinocarbonyl)amino]-N-(3-chlorophenyl)-N′-hydroxy-1,2,5-oxadiazole-3-carboximidamide

4-[(anilinocarbonyl)amino]-N-(3-chlorophenyl)-N′-hydroxy-1,2,5-oxadiazole-3-carboximidamide

Yield 38.0%

Solvents

ethanol

water

Conditions

Workup

1. 1
   OtherPurification of the crude
2. 2
   Otherreaction mixture by preparative HPLC

Procedure

A solution of N-{4-[4-(3-chlorophenyl)-5-oxo-4,5-dihydro-1,2,4-oxadiazol-3-yl]-1,2,5-oxadiazol-3-yl}-N′-phenylurea (17 mg, 43 μmol) in ethanol (1.5 mL) was treated with 2.0 M sodium hydroxide in water (0.3 mL) and stirred for 30 min. Purification of the crude reaction mixture by preparative HPLC gave the desired product 4-[(anilinocarbonyl)amino]-N-(3-chlorophenyl)-N′-hydroxy-1,2,5-oxadiazole-3-carboximidamide (6 mg, 38%). LCMS for C16H14ClN6O3 (M+H)+: m/z=373.0.

Source