Dimethylformamide → HCID 18509436, compound

HRID 1356784Notes

Reaction equation

HRID 1356784 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][CH:10]=1)[CH2:5]CN.C(=O)([O-])[O-].[Na+].[Na+].Br[CH2:18][CH:19]=[CH:20][C:21]#[C:22][C:23]([CH3:26])([CH3:25])[CH3:24].[CH3:27][N:28](C)C=O>>[CH3:24][C:23]([CH3:26])([CH3:25])[C:22]#[C:21]/[CH:20]=[CH:19]/[CH2:18][N:28]([CH2:5][C:4]1[CH:8]=[CH:9][CH:10]=[C:2]([Br:1])[CH:3]=1)[CH3:27]

Participants

5

Reactant 4

HCID 6228Dimethylformamide2×HCID 10340Sodium CarbonateHCID 70217363-BromophenethylamineHCID 454895941-Bromo-6,6-dimethylhept-2-en-4-yne

Product 1

HCID 18509436HCID 18509436, compoundYield 53.8%

Procedure

N-(3-bromobenzyl)methylamine (2.00 g; 10.0 mmol) and sodium carbonate (1.51 g; 14.3 mmol) were added to N,N-dimethylformamide (20 ml). While the mixture was stirred at room temperature, 1-bromo-6,6-dimethyl-2-hepten-4-yne (1.92 g; 9.52 mmol) in N,N-dimethylformamide (10 ml) was added dropwise. The mixture was stirred for 1 hour at room temperature, and the reaction was stopped by pouring the mixture into ice/water, followed by extraction with ethyl acetate (100 ml). The organic layer was washed with saturated aqueous sodium bicarbonate solution and 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=20:1), to thereby yield 1.64 g of the target compound as yellow oily matter (yield: 53.8%).

Workup

  1. stirringThe mixture was stirred for 1 hour at room temperature
  2. extractionfollowed by extraction with ethyl acetate (100 ml)
  3. washThe organic layer was washed with saturated aqueous sodium bicarbonate solution and with saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customThe solvent was evaporated under reduced pressure
  6. customthe residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=20:1)

Sources & evidence

ORD record
ord-5dd763918c8c476d98304e26957eb987
Source dataset
uspto-grants-2003_07
Patent number
US06586633B1

Reaction notes

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