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

HRID 345029
Notes
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Reaction equation

HRID 345029 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
ParticipantsProcedureWorkupSources & evidenceReaction notes

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 6342
Acetonitrile
Solvent

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. 'H-N.m.r. (CDC13): δ=8.6 (d, 1H); 8.3 (dd, 1H); 8.1 (d, 2H); 7.6 (d, 1H); 7.35 (d, 2H); 3.95 (s, 2H); 2.95 (q, 2H); 2.85 (q, 2H); 2.5 (s, 3H) p.p.m.

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-16a4d8d778994655bd85a543ff7226e3
Source dataset
uspto-grants-1991_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05055473

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes