4-Nitroaniline → N-(4-nitrophenyl)-1H-benzimidazol-2-amine
Reaction equation
Cl[C:2]1[NH:3][C:4]2[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=2[N:6]=1.[N+:11]([C:14]1[CH:20]=[CH:19][C:17]([NH2:18])=[CH:16][CH:15]=1)([O-:13])=[O:12]>CN1C(=O)CCC1.C(OCC)(=O)C>[N+:11]([C:14]1[CH:20]=[CH:19][C:17]([NH:18][C:2]2[NH:3][C:4]3[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=3[N:6]=2)=[CH:16][CH:15]=1)([O-:13])=[O:12]Participants
5
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 120 °C
Procedure
A mixture of 2-chlorobenzimidazole (10.0 g) and 4-nitroaniline (9.05 g) in NMP (130 mL) was stirred at 120° C. for 3 days. After this time, the reaction mixture was cooled to ambient temperature, diluted with ethyl acetate (750 mL) and washed with water (750 mL). The aqueous layer was extracted with ethyl acetate (750 mL) and the combined organic extracts were washed with water (3×750 mL) then brine (750 mL), dried over sodium sulfate, and filtered and the filtrate was concentrated under reduced pressure. The residue obtained was triturated with 1:1 ethyl acetate/heptane (200 mL) and the solid that formed was collected by filtration to afford N-(4-nitrophenyl)-1H-benzimidazol-2-amine (4.00 g) as an orange solid.
Workup
- temperatureAfter this time, the reaction mixture was cooled to ambient temperature
- washwashed with water (750 mL)
- extractionThe aqueous layer was extracted with ethyl acetate (750 mL)
- washthe combined organic extracts were washed with water (3×750 mL)
- dry with materialbrine (750 mL), dried over sodium sulfate
- filtrationfiltered
- concentrationthe filtrate was concentrated under reduced pressure
- customThe residue obtained
- customwas triturated with 1:1 ethyl acetate/heptane (200 mL)
- customthe solid that formed
- filtrationwas collected by filtration
Sources & evidence
- ORD record
- ord-c1f95e63453d4395bfd5877bf425e644
- Source dataset
- uspto-grants-2016_01
- Patent number
- US09226921B2
Reaction notes
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