4-Bromobenzyl bromide → 1-(4-Bromo-benzyl)-3-methyl-1,3-dihydro-benzoimidazol-2-ylideneamine
Reaction equation
[CH3:1][N:2]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[NH:4][C:3]1=[NH:11].[Br:12][C:13]1[CH:20]=[CH:19][C:16]([CH2:17]Br)=[CH:15][CH:14]=1>CC(=O)CC>[Br:12][C:13]1[CH:20]=[CH:19][C:16]([CH2:17][N:4]2[C:5]3[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=3[N:2]([CH3:1])[C:3]2=[NH:11])=[CH:15][CH:14]=1Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 90 °C
Procedure
To a solution of 1-methyl-1,3-dihydro-benzoimidazol-2-ylideneamine (0.30 g, 2.04 mmol) in 2-butanone (30 ml) was added 4-bromobenzyl bromide (0.70 g, 2.81 mmol). The reaction was heated to 90° C. where it was stirred for 30 min. After this time, the resulting suspension was cooled to rt and filtered. The collected solids were partitioned between dichloromethane and a saturated solution of NaHCO3 and the mixture was stirred for 10 min. The organic layer was separated and the aqueous phase was extracted with additional dichloromethane. The organic fractions were combined, washed with H2O, dried (Na2SO4), filtered and the filtrate was concentrated under reduced pressure to give 1-(4-bromo-benzyl)-3-methyl-1,3-dihydro-benzoimidazol-2-ylideneamine as a white solid (0.39 g, 61%). HPLC-MS 316, 318 [M+1]+.
Workup
- temperatureAfter this time, the resulting suspension was cooled to rt
- filtrationfiltered
- customThe collected solids were partitioned between dichloromethane
- stirringa saturated solution of NaHCO3 and the mixture was stirred for 10 min
- customThe organic layer was separated
- extractionthe aqueous phase was extracted with additional dichloromethane
- washwashed with H2O
- dry with materialdried (Na2SO4)
- filtrationfiltered
- concentrationthe filtrate was concentrated under reduced pressure
Sources & evidence
- ORD record
- ord-cbc38494ede04e8f8a597965f6860ba8
- Source dataset
- uspto-grants-2014_06
- Patent number
- US08759520B2
Reaction notes
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