2-hydroxy-5-methyl-N-(2-methoxycarbonylbenzylidene)aniline → Methyl 2-(5-methylbenzoxazol-2-yl)benzoate

HRID 273742Notes

Reaction equation

HRID 273742 reaction equation
C([O-])(=O)C.C([O-])(=O)C.C([O-])(=O)C.C([O-])(=O)C.[Pb+4].[OH:18][C:19]1[CH:36]=[CH:35][C:34]([CH3:37])=[CH:33][C:20]=1[N:21]=[CH:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1[C:29]([O:31][CH3:32])=[O:30]>C(Cl)(Cl)Cl>[CH3:37][C:34]1[CH:35]=[CH:36][C:19]2[O:18][C:22]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=3[C:29]([O:31][CH3:32])=[O:30])=[N:21][C:20]=2[CH:33]=1

Participants

4

Reactant 2

HCID 200942472-hydroxy-5-methyl-N-(2-methoxycarbonylbenzylidene)anilineHCID 178418268HCID 178418268, compound

Product 1

HCID 20094237Methyl 2-(5-methylbenzoxazol-2-yl)benzoateYield 64.7%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Lead tetraacetate (16.6 g) was added portionwise to a solution of compound B (8.1 g) in chloroform (150 ml) and the mixture was stirred for 2 hours. Insoluble material was removed by filtration and the filtrate was washed with water (3×50 ml), followed by saturated sodium chloride solution (50 ml), and then dried (MgSO4). The solvent was removed by evaporation and the residue was purified by flash chromatography, eluting with ethyl acetate/hexane (1:9 v/v), to give methyl 2-(5-methylbenzoxazol-2-yl)benzoate (C) (5.2 g), as an oil; NMR: 2.5(s, 3H), 3.85(s, 3H), 7.2(dd, 1H), 7.45(d, 1H), 7.55-7.7(m, 3H), 7.75-7.8(m, 1H), 8.05-8.1(m, 1H).

Workup

  1. customInsoluble material was removed by filtration
  2. washthe filtrate was washed with water (3×50 ml)
  3. dry with materialdried (MgSO4)
  4. customThe solvent was removed by evaporation
  5. customthe residue was purified by flash chromatography
  6. washeluting with ethyl acetate/hexane (1:9 v/v)

Sources & evidence

ORD record
ord-4c67ab3f44d74e2b9ab83d0a16dcbc58
Source dataset
uspto-grants-1995_02
Patent number
US05387592

Reaction notes

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