Dimethylformamide → HCID 18509466, compound

HRID 1356851Notes

Reaction equation

HRID 1356851 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([Br:11])[CH:10]=1)[CH2:5]CN.C(=O)([O-])[O-].[Na+].[Na+].[C:18]([C:22]1[CH:29]=[CH:28][C:25]([CH2:26]Br)=[CH:24][CH:23]=1)([CH3:21])([CH3:20])[CH3:19].[CH3:30][N:31](C)C=O>>[C:18]([C:22]1[CH:29]=[CH:28][C:25]([CH2:26][N:31]([CH2:5][C:4]2[CH:8]=[C:9]([Br:11])[CH:10]=[C:2]([Br:1])[CH:3]=2)[CH3:30])=[CH:24][CH:23]=1)([CH3:21])([CH3:20])[CH3:19]

Participants

5

Reactant 4

HCID 6228Dimethylformamide2×HCID 10340Sodium CarbonateHCID 878361-(Bromomethyl)-4-(1,1-dimethylethyl)benzeneHCID 18509414HCID 18509414, compound

Product 1

HCID 18509466HCID 18509466, compoundYield 66.4%

Procedure

N-(3,5-dibromobenzyl)methylamine (4.38 g; 15.7 mmol) and sodium carbonate (2.37 g; 22.4 mmol) were added to N,N-dimethylformamide (40 ml). While the mixture was stirred at room temperature, p-tert-butylbenzyl bromide (3.40 g; 14.9 mmol) in N,N-dimethylformamide (20 ml) was added dropwise. After completion of the addition, the mixture was stirred for 100 minutes at 50° C., and left to cool to room temperature. The mixture was poured into ice+saturated aqueous sodium bicarbonate solution, followed by extraction with diethyl ether (100 ml). The organic layer was washed with saturated aqueous sodium bicarbonate solution, and extracted with 2N hydrochloric acid twice (100 ml each). Crystals that precipitated were collected, and combined with the aqueous layer. The mixture was alkalinized with aqueous sodium hydroxide solution, and extracted with chloroform (100 ml). The organic layer was washed with water and then with saturated brine, and dried over sodium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=40:1), to thereby yield 4.21 g of the target compound as pale white oily matter (yield: 66.4%).

Workup

  1. additionAfter completion of the addition
  2. stirringthe mixture was stirred for 100 minutes at 50° C.
  3. waitleft
  4. temperatureto cool to room temperature
  5. additionThe mixture was poured into ice+saturated aqueous sodium bicarbonate solution
  6. extractionfollowed by extraction with diethyl ether (100 ml)
  7. washThe organic layer was washed with saturated aqueous sodium bicarbonate solution
  8. extractionextracted with 2N hydrochloric acid twice (100 ml each)
  9. customCrystals that precipitated
  10. customwere collected
  11. extractionextracted with chloroform (100 ml)
  12. washThe organic layer was washed with water
  13. dry with materialwith saturated brine, and dried over sodium sulfate
  14. customThe solvent was evaporated under reduced pressure
  15. customthe residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=40:1)

Sources & evidence

ORD record
ord-65cbf11b1288439a8513f22c782adeec
Source dataset
uspto-grants-2003_07
Patent number
US06586633B1

Reaction notes

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