1,1-Dimethoxyethyl(dimethyl)amine → 3-(2-Bromo-4-chloro-6-fluorophenyl)-5-methyl-1,2,4-oxadiazole
Reaction equation
[Br:1][C:2]1[CH:11]=[C:10]([Cl:12])[CH:9]=[C:8]([F:13])[C:3]=1[C:4]([NH:6][OH:7])=[NH:5].CO[C:16](OC)(N(C)C)[CH3:17]>CC(O)C>[Br:1][C:2]1[CH:11]=[C:10]([Cl:12])[CH:9]=[C:8]([F:13])[C:3]=1[C:4]1[N:5]=[C:16]([CH3:17])[O:7][N:6]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of 2-bromo-4-chloro-6-fluoro-N-hydroxy-benzamidine (26.5 g, 99.25 mmol) in 2-propanol (200 ml) was added N,N-dimethylacetamide dimethyl acetal (35.2 ml, 238.20 mmol) slowly at 25° C. and the reaction mixture was stirred for 30 minutes. After completion of the reaction all volatiles were evaporated and the resulting crude product was purified by chromatography (silica gel; hexane/EtOAc 97:3) to obtain the title compound as white solid (27.5 g, 58%). MS: m/z=290 [M]+.