1-Chloro-4-nitrobenzene → HCID 12874832, compound

HRID 848513Notes

Reaction equation

HRID 848513 reaction equation
[H-].[Na+].Cl.[CH3:4][N:5]([CH3:16])[CH2:6][CH2:7][CH:8]([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[OH:9].Cl[C:18]1[CH:23]=[CH:22][C:21]([N+:24]([O-:26])=[O:25])=[CH:20][CH:19]=1>CS(C)=O>[CH3:16][N:5]([CH3:4])[CH2:6][CH2:7][CH:8]([O:9][C:18]1[CH:23]=[CH:22][C:21]([N+:24]([O-:26])=[O:25])=[CH:20][CH:19]=1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

5

Reactant 3

HCID 74741-Chloro-4-nitrobenzeneHCID 24758Sodium hydrideHCID 2770479AC1MCIJF

Product 1

HCID 12874832HCID 12874832, compoundYield 95.4%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
22 °C

Procedure

26 ml of dimethylsulfoxide were added to 2.6 g of a 50% dispersion of sodium hydride in oil and the mixture was stirred at 60°-65° C. for 30 minutes and was then cooled to 22° C. 5.8 g of N,N-dimethyl-3-phenyl-3-hydroxy-propanamine hydrochloride were added to the mixture which was then stirred for 10 minutes at 25° C. Then, 8.95 g of p-chloronitrobenzene were added to the mixture which was stirred at room temperature for 15 minutes. The mixture was extracted with methylene chloride and the organic phase was washed with water, dried, filtered and evaporated to dryness under reduced pressure to obtain 17 g of raw product. The latter was extracted 3 times with 200 ml of N hydrochloric acid and the neutral fraction was eliminated 3 times with 200 ml of ether. The combined aqueous phases were made alkaline with excess concentrated ammonium hydroxide and the precipitate was extracted with methylene chloride. The extract was dried, filtered and evaporated to dryness under reduced pressure to obtain 7.7 g of N,N-dimethyl-γ-(4-nitrophenoxy)benzene-propanamine.

Workup

  1. stirringwas then stirred for 10 minutes at 25° C
  2. stirringwas stirred at room temperature for 15 minutes
  3. extractionThe mixture was extracted with methylene chloride
  4. washthe organic phase was washed with water
  5. customdried
  6. filtrationfiltered
  7. customevaporated to dryness under reduced pressure
  8. customto obtain 17 g of raw product
  9. extractionThe latter was extracted 3 times with 200 ml of N hydrochloric acid
  10. extractionthe precipitate was extracted with methylene chloride
  11. customThe extract was dried
  12. filtrationfiltered
  13. customevaporated to dryness under reduced pressure

Sources & evidence

ORD record
ord-bfc60e07aa4f45f8b1d44bfad5e85da5
Source dataset
uspto-grants-1981_10
Patent number
US04296126

Reaction notes

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