Sodium Iodide → N-Methyl-2-(4-nitrophenoxy)-N-[2-(4-nitrophenyl)ethyl]ethanamine

HRID 1089692Notes

Reaction equation

HRID 1089692 reaction equation
[CH3:1][NH:2][CH2:3][CH2:4][C:5]1[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[CH:7][CH:6]=1.[N+:14]([C:17]1[CH:26]=[CH:25][C:20]([O:21][CH2:22][CH2:23]Cl)=[CH:19][CH:18]=1)([O-:16])=[O:15].C(=O)([O-])[O-].[K+].[K+].[I-].[Na+]>C(#N)C>[N+:14]([C:17]1[CH:26]=[CH:25][C:20]([O:21][CH2:22][CH2:23][N:2]([CH3:1])[CH2:3][CH2:4][C:5]2[CH:6]=[CH:7][C:8]([N+:11]([O-:13])=[O:12])=[CH:9][CH:10]=2)=[CH:19][CH:18]=1)([O-:16])=[O:15]

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 27645871-(2-Chloroethoxy)-4-nitrobenzeneHCID 2794239N-methyl-4-nitrophenethylamine

Product 1

HCID 14645090N-Methyl-2-(4-nitrophenoxy)-N-[2-(4-nitrophenyl)ethyl]ethanamineYield 71.6%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of N-methyl-4-nitrophenethylamine (1.5 g) (J.O.C., [1956], 21, 45) and 2-[4-nitrophenoxy]ethyl chloride (1.55 g) (C.A., [1955], 49, 3163e) in acetonitrile (50 ml) was added potassium carbonate (1.25 g) and sodium iodide (1.2 g) and the suspension was stirred at reflux for 72 hours. After evaporation to dryness, the residual oily solid was partitioned between a 2N aqueous sodium bicarbonate solution and ethyl acetate. After two further extractions with ethyl acetate, the organic portions were combined, washed with a saturated aqueous brine solution, dried over magnesium sulphate, filtered and evaporated. The resultant orange solid (2.7 g) was crystallised from ethanol to give the title compound, (1.9 g), m.p. 74°.

Workup

  1. temperatureat reflux for 72 hours
  2. customAfter evaporation to dryness
  3. customthe residual oily solid was partitioned between a 2N aqueous sodium bicarbonate solution and ethyl acetate
  4. extractionAfter two further extractions with ethyl acetate
  5. washwashed with a saturated aqueous brine solution
  6. dry with materialdried over magnesium sulphate
  7. filtrationfiltered
  8. customevaporated
  9. customThe resultant orange solid (2.7 g) was crystallised from ethanol

Sources & evidence

ORD record
ord-91fab6aa68ab4c589c269b6e156c7fef
Source dataset
uspto-grants-1992_01
Patent number
US05079248

Reaction notes

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