Hydrochloric Acid → 6-Bromo-1-(3-methoxypropyl)-2-trifluoromethyl-1H-benzoimidazole

반응식

Cl.[Br:2][C:3]1[CH:4]=[C:5]([NH:10][CH2:11][CH2:12][CH2:13][O:14][CH3:15])[C:6]([NH2:9])=[CH:7][CH:8]=1.C(=O)([O-])O.[Na+].[F:21][C:22]([F:27])([F:26])[C:23](O)=O>>[Br:2][C:3]1[CH:8]=[CH:7][C:6]2[N:9]=[C:23]([C:22]([F:27])([F:26])[F:21])[N:10]([CH2:11][CH2:12][CH2:13][O:14][CH3:15])[C:5]=2[CH:4]=1

참가 물질

반응물 4

HCID 313Hydrochloric Acid

HCID 6422Trifluoroacetic acid2회

HCID 516892Sodium Bicarbonate

HCID 653434125-bromo-N1-(3-methoxypropyl)benzene-1,2-diamine

생성물 1

HCID 668885926-Bromo-1-(3-methoxypropyl)-2-trifluoromethyl-1H-benzoimidazole

실험 절차

0.2 ml of concentrated aqueous hydrochloric acid is added under an argon atmosphere to a solution of 12.83 g of 4-bromo-N2-(3-methoxypropyl)benzene-1,2-diamine in 5.78 ml of trifluoroacetic acid. The reaction mixture is heated to reflux for 4 hours. 2 ml of trifluoroacetic acid are once again added and the reaction mixture is heated to reflux for a further 2 hours. The reaction mixture is cooled to room temperature and neutralized with saturated aqueous sodium hydrogencarbonate solution. The mixture is extracted with ethyl acetate (3×). The combined organic phases are dried over sodium sulphate and concentrated by evaporation. The title compound is obtained as a yellow oil from the residue by means of flash chromatography (SiO2 60F). Rf=0.60 (1:2 EtOAc-heptane). Rt=4.79 (gradient I).