Sodium Iodide → N-methyl-N-(5-nitrobenzoxazol-2-ylmethyl)-4-nitrophenethylamine

HRID 467087Notes

Reaction equation

HRID 467087 reaction equation
Cl[CH2:2][C:3]1[O:4][C:5]2[CH:11]=[CH:10][C:9]([N+:12]([O-:14])=[O:13])=[CH:8][C:6]=2[N:7]=1.[CH3:15][NH:16][CH2:17][CH2:18][C:19]1[CH:24]=[CH:23][C:22]([N+:25]([O-:27])=[O:26])=[CH:21][CH:20]=1.C(=O)([O-])[O-].[K+].[K+].[I-].[Na+]>C(#N)C>[CH3:15][N:16]([CH2:17][CH2:18][C:19]1[CH:24]=[CH:23][C:22]([N+:25]([O-:27])=[O:26])=[CH:21][CH:20]=1)[CH2:2][C:3]1[O:4][C:5]2[CH:11]=[CH:10][C:9]([N+:12]([O-:14])=[O:13])=[CH:8][C:6]=2[N:7]=1

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 27641892-(Chloromethyl)-5-nitro-1,3-benzoxazoleHCID 2794239N-methyl-4-nitrophenethylamine

Product 1

HCID 19813428N-methyl-N-(5-nitrobenzoxazol-2-ylmethyl)-4-nitrophenethylamine

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

2-Chloromethyl-5-nitrobenzoxazole (2.85 g, 13.4 mmole), N-methyl-4-nitrophenethylamine (J. O. C., [1956], 21, 45) (2.2 g, 12.2 mmole), potassium carbonate (1.85 g, 13.4 mmole) and sodium iodide (2.0 g, 13.4 mmole) were heated under reflux in acetonitrile (50 ml) for 3 days. The solvent was then evaporated, the residue diluted with water, and extracted three times with methylene chloride. The combined organic extracts were washed with water, dried (MgSO4), filtered and evaporated to dryness. The resultant oil was diluted with ether and the supernatant decanted and evaporated to dryness to give an orange solid, which was recrystallised from isopropanol to give the title compound, yield 0.80 g.

Workup

  1. customThe solvent was then evaporated
  2. additionthe residue diluted with water
  3. extractionextracted three times with methylene chloride
  4. washThe combined organic extracts were washed with water
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. customevaporated to dryness
  8. additionThe resultant oil was diluted with ether
  9. customthe supernatant decanted
  10. customevaporated to dryness
  11. customto give an orange solid, which
  12. customwas recrystallised from isopropanol

Sources & evidence

ORD record
ord-fccd1f9729ea47bca77dd8c2d549353b
Source dataset
uspto-grants-1992_10
Patent number
US05158964

Reaction notes

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