Dimethylformamide → HCID 18509519, compound
Reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:11])=[C:6]([CH:10]=1)[CH2:7]CN.C(=O)([O-])[O-].[Na+].[Na+].Br[CH2:19][CH:20]=[CH:21][C:22]#[C:23][C:24]([CH3:27])([CH3:26])[CH3:25].[CH3:28][N:29](C)C=O>>[CH3:25][C:24]([CH3:27])([CH3:26])[C:23]#[C:22]/[CH:21]=[CH:20]/[CH2:19][N:29]([CH2:7][C:6]1[CH:10]=[C:2]([Br:1])[CH:3]=[CH:4][C:5]=1[CH3:11])[CH3:28]Participants
Procedure
N-(5-bromo-2-methylbenzyl)methylamine (2.89 g; 13.5 mmol) and sodium carbonate (1.50 g; 14.2 mmol) were added to N,N-dimethylformamide (25 ml). While the mixture was stirred at room temperature, 1-bromo-6,6-dimethyl-2-hepten-4-yne (2.71 g; 13.5 mmol) in N,N-dimethylformamide (5 ml) was added dropwise. The mixture was stirred for 21 hours at room temperature, and concentrated under reduced pressure. Water was added to the residue, and the mixture was extracted with ether (150 ml). The organic layer was washed with saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=50:1), to thereby yield 1.10 g of the target compound as orange oily matter (yield: 24.4%).
Workup
- stirringThe mixture was stirred for 21 hours at room temperature
- concentrationconcentrated under reduced pressure
- additionWater was added to the residue
- extractionthe mixture was extracted with ether (150 ml)
- washThe organic layer was washed with saturated brine
- dry with materialdried over anhydrous sodium sulfate
- customThe solvent was evaporated under reduced pressure
- customthe residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=50:1)
Sources & evidence
- ORD record
- ord-01ccf37a56504aedafc9ebce921649c1
- Source dataset
- uspto-grants-2003_07
- Patent number
- US06586633B1
Reaction notes
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