Hydrochloric Acid → 6-Bromo-1-(3-methoxypropyl)-2-trifluoromethyl-1H-benzoimidazole
Reaction equation
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]=1Participants
Procedure
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).
Workup
- temperatureThe reaction mixture is heated
- temperatureto reflux for 4 hours
- temperaturethe reaction mixture is heated
- temperatureto reflux for a further 2 hours
- extractionThe mixture is extracted with ethyl acetate (3×)
- dry with materialThe combined organic phases are dried over sodium sulphate
- concentrationconcentrated by evaporation
Sources & evidence
- ORD record
- ord-a7d92651382346e5a3c3145952562ebf
- Source dataset
- uspto-grants-2011_01
- Patent number
- US07868036B2
Reaction notes
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