Thionyl Chloride → 1-{4-[4-(Chloromethyl)-5-methyl-1,3-oxazol-2-yl]benzyl}-1H-benzimidazole
Reaction equation
[N:1]1([CH2:10][C:11]2[CH:16]=[CH:15][C:14]([C:17]3[O:18][C:19]([CH3:24])=[C:20]([CH2:22]O)[N:21]=3)=[CH:13][CH:12]=2)[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[CH:2]1.S(Cl)([Cl:27])=O>C(Cl)Cl>[Cl:27][CH2:22][C:20]1[N:21]=[C:17]([C:14]2[CH:15]=[CH:16][C:11]([CH2:10][N:1]3[C:5]4[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=4[N:3]=[CH:2]3)=[CH:12][CH:13]=2)[O:18][C:19]=1[CH3:24]Participants
4
Procedure
A solution of {2-{4-[(1H-benzimidazol-1-yl)methyl]phenyl}-5-methyl-1,3-oxazole-4-yl}methanol (0.045 g, 0.14 mmol) in CH2Cl2 was treated with a solution of thionyl chloride (0.10 mL, 1.4 mmol) in CH2Cl2 (2 mL), heated to reflux temperature, stirred for 30 min, cooled to room temperature and concentrated in vacuo. The resultant residue was partitioned between CH2Cl2 and water. The organic phase was separated, washed with water, brine, dried over Na2SO4, and evaporated to dryness under reduced pressure to give the title product, LCMS (ESI+) 337 (MH+).