Sodium Iodide → HCID 19915727, compound

HRID 1032670Notes

Reaction equation

HRID 1032670 reaction equation
[CH3:1][NH:2][CH2:3][CH2:4][C:5]1[CH:10]=[CH:9][C:8]([NH:11][S:12]([CH3:15])(=[O:14])=[O:13])=[CH:7][CH:6]=1.[N+:16]([C:19]1[CH:28]=[CH:27][C:22]([O:23][CH2:24][CH2:25]Br)=[CH:21][CH:20]=1)([O-:18])=[O:17].C(=O)([O-])[O-].[K+].[K+].[I-].[Na+]>C(#N)C>[N+:16]([C:19]1[CH:28]=[CH:27][C:22]([O:23][CH2:24][CH2:25][N:2]([CH3:1])[CH2:3][CH2:4][C:5]2[CH:6]=[CH:7][C:8]([NH:11][S:12]([CH3:15])(=[O:14])=[O:13])=[CH:9][CH:10]=2)=[CH:21][CH:20]=1)([O-:18])=[O:17]

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 2359871-(2-Bromoethoxy)-4-nitrobenzeneHCID 10036749HCID 10036749, compound

Product 1

HCID 19915727HCID 19915727, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of N-methyl-4-methanesulphonamidophenethylamine (1.0 g) (see Preparation 8), 2-(4-nitrophenoxy)ethyl bromide (1.2 g) (C.A., 54, 11046a), potassium carbonate (0.67 g) and sodium iodide (0.72 g) in acetonitrile (100 ml) was stirred at reflux for 3 days. On evaporation to dryness, the residual oil was partitioned between water and methylene chloride. After two further extractions with methylene chloride, the organic portions were combined, washed with saturated brine solution, dried over anhydrous magnesium sulphate, filtered and evaporated to dryness. The resultant yellow oil was taken up in hot methanol, cooled and the title compound crystallised as a colourless solid, (1.2 g).

Workup

  1. temperatureat reflux for 3 days
  2. customOn evaporation to dryness
  3. customthe residual oil was partitioned between water and methylene chloride
  4. extractionAfter two further extractions with methylene chloride
  5. washwashed with saturated brine solution
  6. dry with materialdried over anhydrous magnesium sulphate
  7. filtrationfiltered
  8. customevaporated to dryness
  9. temperaturecooled
  10. customthe title compound crystallised as a colourless solid, (1.2 g)

Sources & evidence

ORD record
ord-46e87392126d45b3b4ff439aa5e61da7
Source dataset
uspto-grants-1990_09
Patent number
US04959366

Reaction notes

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