Hydrochloric Acid → 1-(4-Nitrobenzyl)-3-(4-trifluoromethoxybenzyl)-1,3-dihydrobenzimidazol-2-one
Reaction equation
[F:1][C:2]([F:22])([F:21])[O:3][C:4]1[CH:20]=[CH:19][C:7]([CH2:8][N:9]2[C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=3[NH:11][C:10]2=[O:18])=[CH:6][CH:5]=1.[N+:23]([C:26]1[CH:33]=[CH:32][C:29]([CH2:30]Br)=[CH:28][CH:27]=1)([O-:25])=[O:24].C(=O)([O-])[O-].[K+].[K+].[I-].[K+].Cl>O.CN(C=O)C>[N+:23]([C:26]1[CH:33]=[CH:32][C:29]([CH2:30][N:11]2[C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=3[N:9]([CH2:8][C:7]3[CH:19]=[CH:20][C:4]([O:3][C:2]([F:1])([F:21])[F:22])=[CH:5][CH:6]=3)[C:10]2=[O:18])=[CH:28][CH:27]=1)([O-:25])=[O:24]Participants
8
Reactant 5
Product 1
Reagents, catalysts & solvents 2
Procedure
To a solution of compound R (770 mg, 2.5 mmol) in abs. DMF (20 mL) there were added 4-nitrobenzyl bromide (540 mg, 2.5 mmol), potassium carbonate (828 mg, 6 mmol), and a catalytic amount of potassium iodide under a blanket of argon. The reaction mixture was heated to from 80° to 85° C. over a period of 5 h. Following cooling, the reaction mixture was poured into a mixture of ice (200 g) and 2N hydrochloric acid solution in H2O (10 mL), and the reaction mixture was stirred for 1 hour. The resulting solid matter was separated through a frit and recrystallized from ethanol (20 mL). The desired product 1-(4-nitrobenzyl)-3-(4-trifluoromethoxybenzyl)-1,3-dihydrobenzimidazol-2-one (T) was obtained in a yield of 830 g (74% of theory).
Workup
- temperatureThe reaction mixture was heated to from 80° to 85° C. over a period of 5 h
- temperatureFollowing cooling
- customThe resulting solid matter was separated through a frit
- customrecrystallized from ethanol (20 mL)
Sources & evidence
- ORD record
- ord-1bf4c11e1d9143f8b20c5028f0c6effc
- Source dataset
- uspto-grants-2012_06
- Patent number
- US08207182B2
Reaction notes
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