HCID 13850476, compound → HCID 13850477, compound

HRID 542677Notes

Reaction equation

HRID 542677 reaction equation
[C:1]([C:5]1[CH:31]=[CH:30][CH:29]=[CH:28][C:6]=1[CH:7]=[N:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][C:16]2[CH:21]=[CH:20][C:19]([C:22]([F:25])([F:24])[F:23])=[CH:18][C:17]=2[Cl:26])=[CH:11][C:10]=1[OH:27])([O:3][CH3:4])=[O:2].C([O-])(=O)C.C([O-])(=O)C.C([O-])(=O)C.C([O-])(=O)C.[Pb+4]>C(Cl)(Cl)Cl>[C:1]([C:5]1[CH:31]=[CH:30][CH:29]=[CH:28][C:6]=1[C:7]1[O:27][C:10]2[CH:11]=[C:12]([O:15][C:16]3[CH:21]=[CH:20][C:19]([C:22]([F:25])([F:24])[F:23])=[CH:18][C:17]=3[Cl:26])[CH:13]=[CH:14][C:9]=2[N:8]=1)([O:3][CH3:4])=[O:2]

Participants

4

Reactant 2

HCID 13850476HCID 13850476, compoundHCID 178418268HCID 178418268, compound

Product 1

HCID 13850477HCID 13850477, compoundYield 81.9%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a stirred solution of 2.7 grams (0.006 mole) N-(o-carbomethoxybenzylidene)-2-hydroxy-4-(2-chloro-4-trifluoromethylphenoxy)aniline in 25 ml of chloroform was added portionwise 2.9 grams (0.007 mole) lead tetraacetate. The reaction mixture was stirred for an additional hour, then washed sequentially with three portions of water and an aqueous saturated sodium chloride solution. The organic layer was concentrated under reduced pressure to a residual oil. The oil was dissolved in methylene chloride and passed through a column of activated magnesium silicate. The appropriate fractions were combined and concentrated under reduced pressure to give 2.2 grams of 2-(o-carbomethoxyphenyl)-6-(2-chloro-4-trifluoromethylphenoxy)-benzoxazole as an oil. The nmr spectrum was consistent with the proposed structure.

Workup

  1. washwashed sequentially with three portions of water
  2. concentrationThe organic layer was concentrated under reduced pressure to a residual oil
  3. dissolutionThe oil was dissolved in methylene chloride
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-9311c5bafdc244bfa08f04c518055d96
Source dataset
uspto-grants-1987_04
Patent number
US04659360

Reaction notes

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