Triethyl orthoacetate → 2-(4-Iodophenyl)-5-methyl-[1,3,4]oxadiazole
Reaction equation
[I:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([NH:8][NH2:9])=[O:7])=[CH:4][CH:3]=1.[C:12](OCC)(OCC)(OCC)[CH3:13]>>[I:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]2[O:7][C:12]([CH3:13])=[N:9][N:8]=2)=[CH:4][CH:3]=1Participants
3
Conditions
- Temperature
- 130 °C
Procedure
Triethyl orthoacetate (10 ml) was added to 4-iodo-benzoic acid hydrazide (Intermediate 14) (0.55 g, 2.1 mmol) and heated under nitrogen at 130° C. for 3 hours. The triethyl orthoacetate was removed in vacuo and the residue partitioned between ethyl acetate (30 ml) and water (30 ml). The organic layer was washed with water (50 ml), brine (50 ml), dried over magnesium sulfate filtered and the solvent removed in vacuo. The residue was purified by silica SPE cartridge (10 g) eluting with 20:1 cyclohexane/ethyl acetate v:v to 5:1 cyclohexane/ethyl acetate v:v. The desired product was obtained as a white solid (0.31 g, 1.1 mmol).