Sodium Iodide → HCID 23365874, compound

HRID 275156

Reaction equation

HRID 275156 reaction equation
[N+:1]([C:4]1[CH:5]=[CH:6][C:7]2[O:12][CH2:11][CH2:10][NH:9][C:8]=2[CH:13]=1)([O-:3])=[O:2].Br[CH2:15][C:16]1[CH:17]=[C:18]([CH:23]=[CH:24][CH:25]=1)[C:19]([O:21][CH3:22])=[O:20].C(=O)([O-])[O-].[K+].[K+].[I-].[Na+]>CC(=O)CC>[N+:1]([C:4]1[CH:5]=[CH:6][C:7]2[O:12][CH2:11][CH2:10][N:9]([CH2:15][C:16]3[CH:17]=[C:18]([CH:23]=[CH:24][CH:25]=3)[C:19]([O:21][CH3:22])=[O:20])[C:8]=2[CH:13]=1)([O-:3])=[O:2]

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 517981Methyl 3-(bromomethyl)benzoateHCID 70622256-nitro-3,4-dihydro-2H-1,4-benzoxazine

Product 1

HCID 23365874HCID 23365874, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

A mixture of 6-nitro-2,3-dihydrobenz-1,4-oxazine (0.45 g.), methyl 3-bromomethylbenzoate* (Y) (0.58 g.), potassium carbonate (0.35 g.), and sodium iodide (0.38 g.) in dry 2 -butanone (25 ml.) was stirred and heated under reflux for 48 hours. The cooled reaction mixture was filtered, the filter cake washed with 2-butanone, and the combined filtrate evaporated. The product was purified by flash chromatography on silica gel, eluting with 5:95 v/v ethyl acetate:toluene to give methyl 3-(6-nitro-2,3-dihydrobenz-1,4-oxazin-4-ylmethyl)benzoate (0.7 g., 85%) as a yellow oil; partial NMR (80 MHz, CDCl3): 3.5(m,2H, N.CH2.CH2O); 3.9(s,3H, OMe); 4.3(m,2H, N.CH2.CH2O); 4.6(s,2H, NCH2Ar).

Workup

  1. temperatureheated
  2. temperatureunder reflux for 48 hours
  3. customThe cooled reaction mixture
  4. filtrationwas filtered
  5. washthe filter cake washed with 2-butanone
  6. customthe combined filtrate evaporated
  7. customThe product was purified by flash chromatography on silica gel
  8. washeluting with 5:95 v/v ethyl acetate

Sources & evidence

ORD record
ord-01cf757aae454869b671e8ce81965cb2
Source dataset
uspto-grants-1995_02
Patent number
US05391758

Linked notes

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