Sodium hydride → 1-(3,4-dinitrophenoxy)-2-[N-(3,4-dimethoxyphenethyl)-N-methylamino]ethane hydrochloride

HRID 1106863Notes

Reaction equation

HRID 1106863 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:13]=[CH:14][C:15]=1[O:16][CH3:17])[CH2:6][CH2:7][N:8]([CH2:10][CH2:11][OH:12])[CH3:9].[H-].[Na+].[Cl:20][C:21]1[CH:26]=[CH:25][C:24]([N+:27]([O-:29])=[O:28])=[C:23]([N+:30]([O-:32])=[O:31])[CH:22]=1>CS(C)=O>[ClH:20].[N+:27]([C:24]1[CH:25]=[C:26]([CH:21]=[CH:22][C:23]=1[N+:30]([O-:32])=[O:31])[O:12][CH2:11][CH2:10][N:8]([CH2:7][CH2:6][C:5]1[CH:13]=[CH:14][C:15]([O:16][CH3:17])=[C:3]([O:2][CH3:1])[CH:4]=1)[CH3:9])([O-:29])=[O:28]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 330974-Chloro-1,2-dinitrobenzeneHCID 144073182-((3,4-Dimethoxyphenethyl)(methyl)amino)ethanol

Product 1

HCID 187899401-(3,4-dinitrophenoxy)-2-[N-(3,4-dimethoxyphenethyl)-N-methylamino]ethane hydrochlorideYield 33.4%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A portion (0.50 g, 2.1 mmol) of the 2-[N-(3,4-dimethoxyphenethyl)-N-methylamino]ethanol produced in (1) above was dissolved in dimethyl sulfoxide (6 ml) and 60% sodium hydride (0.12 g, 3 mmol) was added to the resulting solution. The reaction mixture was stirred at room temperature for 1 h and 1-chloro-3,4-dinitrobenzene (0.48 ml, 4 mmol) was added on a water bath. The mixture was stirred at room temperature for 2 h and after adding a saturated aqueous solution of sodium bicarbonate, three extractions were conducted with chloroform. The organic layers were combined, dried with sodium sulfate and concentrated under vacuum. The residue was purified by being subjected to column chromatography on silica gel using a 15:1 solvent system of chloroform and methanol as an eluent and the fractions containing the end compound were collected and the solvent was evaporated under vacuum, with the residue being recrystallized from ethanol to yield the titled compound 1-(3,4-dinitrophenoxy)-2-[N-(3,4-dimethoxyphenethyl)-N-methylamino]ethane hydrochloride (0.31 g).

Workup

  1. stirringThe mixture was stirred at room temperature for 2 h
  2. additionafter adding
  3. extractiona saturated aqueous solution of sodium bicarbonate, three extractions
  4. dry with materialdried with sodium sulfate
  5. concentrationconcentrated under vacuum
  6. customThe residue was purified
  7. additionthe fractions containing the end compound
  8. customwere collected
  9. customthe solvent was evaporated under vacuum, with the residue
  10. custombeing recrystallized from ethanol

Sources & evidence

ORD record
ord-1fea8472b6644f14a44962036196c71d
Source dataset
uspto-grants-2000_05
Patent number
US06057358

Reaction notes

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