Sodium hydride → HCID 60207431, compound

HRID 1052465Notes

Reaction equation

HRID 1052465 reaction equation
[CH3:1][N:2]([CH3:7])[CH2:3][CH2:4][CH2:5][OH:6].[H-].[Na+].Cl[C:11]1[CH:16]=[CH:15][C:14]([N+:17]([O-:19])=[O:18])=[CH:13][C:12]=1[O:20][CH3:21]>CS(C)=O.O>[CH3:21][O:20][C:12]1[CH:13]=[C:14]([N+:17]([O-:19])=[O:18])[CH:15]=[CH:16][C:11]=1[O:6][CH2:5][CH2:4][CH2:3][N:2]([CH3:7])[CH3:1]

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 705192-Chloro-5-nitroanisoleHCID 766463-(Dimethylamino)-1-propanol

Product 1

HCID 60207431HCID 60207431, compoundYield 35.6%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolvent2×HCID 962WaterSolvent

Procedure

3-(Dimethylamino)propan-1-ol (1 g, 10.6 mmol) was dissolved in dimethylsulfoxide (20 ml) and sodium hydride (0.42 g, 10.5 mmol) was added. After stirring at room temperature for 15 min, 1-chloro-2-methoxy-4-nitrobenzene (1 g, 5.3 mmol) in dimethylsulfoxide (10 ml) was added and the reaction mixture stirred 4 h at room temperature. The reaction mixture was diluted with water, extracted with ethyl acetate, and the organic phase dried over magnesium sulphate and filtered. After evaporation of the solvent, the residue was purified by flash chromatography using SP1® Purification System (0% to 85%, ethyl acetate-methanol) to obtain 480 mg (34% yield) of the title compound as an oil.

Workup

  1. stirringthe reaction mixture stirred 4 h at room temperature
  2. extractionextracted with ethyl acetate
  3. dry with materialthe organic phase dried over magnesium sulphate
  4. filtrationfiltered
  5. customAfter evaporation of the solvent
  6. customthe residue was purified by flash chromatography
  7. customSP1® Purification System (0% to 85%, ethyl acetate-methanol)

Sources & evidence

ORD record
ord-a6f39893f0414d53afad8dd76ac051cf
Source dataset
uspto-grants-2016_07
Patent number
US09388189B2

Reaction notes

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