Potassium Carbonate → 2-n-Butyl-4-chloro-1-(4-bromobenzyl)-5-formylimidazole
Reaction equation
[CH2:1]([C:5]1[NH:6][C:7]([CH:11]=[O:12])=[C:8]([Cl:10])[N:9]=1)[CH2:2][CH2:3][CH3:4].[Br:13][C:14]1[CH:21]=[CH:20][C:17]([CH2:18]Br)=[CH:16][CH:15]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C(=O)C>[CH2:1]([C:5]1[N:6]([CH2:18][C:17]2[CH:20]=[CH:21][C:14]([Br:13])=[CH:15][CH:16]=2)[C:7]([CH:11]=[O:12])=[C:8]([Cl:10])[N:9]=1)[CH2:2][CH2:3][CH3:4]Participants
Conditions
- Temperature
- -10 °C
Procedure
In 200 ml of N,N-dimethylacetamide (DMAC) were dissolved 31.0 g (0.166 mol) of 2-n-butyl-4-chloro-5-formylimidazole and 41.5 g (0.166 mol) of p-bromobenzyl bromide. After this solution was cooled to -10° C., 23.7 g (0.168 mol) of potassium carbonate particles which had a specific surface area of 1.5 m2 /g and in which the content of particles each having a diameter of 74 μm or smaller was 30% by weight were added to the solution over 10 minutes while holding the solution at -10 to -5° C. The resultant mixture was stirred at -10° C. for 2 hours, subsequently heated to room temperature, and then stirred for 2 hours to complete the reaction (which was conducted in an air atmosphere). Thereafter, the reaction mixture was filtered and the filtrate was cooled to 0° C. Thereto was added 320 ml of 15° C. water. The crystals thus precipitated were taken out by filtration to obtain 55.8 g of 2-n-butyl-4-chloro-1-(4-bromobenzyl)-5-formylimidazole having a purity of 99.8% (yield, 98.0%).
Workup
- additionwere added to the solution over 10 minutes
- customat -10 to -5° C
- temperaturesubsequently heated to room temperature
- customthe reaction (which
- filtrationThereafter, the reaction mixture was filtered
- temperaturethe filtrate was cooled to 0° C
- additionThereto was added 320 ml of 15° C. water
- customThe crystals thus precipitated
- filtrationwere taken out by filtration
Sources & evidence
- ORD record
- ord-703e0fe9399a4e999b6845f844b60046
- Source dataset
- uspto-grants-1999_11
- Patent number
- US05977377
Reaction notes
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