Hydrochloric Acid → HCID 9911206, compound

HRID 584406Notes

Reaction equation

HRID 584406 reaction equation
[H-].[Na+].[OH:3]/[N:4]=[C:5](\[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)/[C:6]([O:8]C)=[O:7].Cl[CH2:17][C:18]1[CH:37]=[CH:36][C:21]([O:22][CH2:23][C:24]2[N:25]=[C:26]([C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)[O:27][C:28]=2[CH3:29])=[CH:20][CH:19]=1.Cl.C(=O)(O)[O-].[Na+]>CN(C)C=O>[CH3:29][C:28]1[O:27][C:26]([C:30]2[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=2)=[N:25][C:24]=1[CH2:23][O:22][C:21]1[CH:20]=[CH:19][C:18]([CH2:17][O:3]/[N:4]=[C:5](\[C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)/[C:6]([OH:8])=[O:7])=[CH:37][CH:36]=1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 516892Sodium BicarbonateHCID 9614877HCID 9614877, compoundHCID 109469404-(4-Chloromethylphenoxy)methyl-5-methyl-2-phenyloxazole

Product 1

HCID 9911206HCID 9911206, compoundYield 70.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Sodium hydride (60%, in oil, 122 mg) was added under a nitrogen atmosphere to a solution of methyl E-2-hydroxyimino-2-phenylacetate (548 mg) and 4-(4-chloromethylphenoxymethyl)-5-methyl-2-phenyloxazole (960 mg) in N,N-dimethylformamide (10 ml) at room temperature and the mixture was stirred for 1 hour. After adding 1N HCl (5 ml), aqueous sodium bicarbonate was added, and then the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated aqueous sodium chloride, dried (MgSO4) and then concentrated. The residue was subjected to column chromatography on silica gel to obtain a colorless oil from a fraction eluted with ethyl acetate-hexane (1:2, v/v). This oil was dissolved in methanol (5 ml)-1N aqueous solution of sodium hydroxide (5 ml) and the mixture was heated under reflux for 3 hours. 1N HCl (5.5 ml) was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated aqueous sodium chloride, dried (MgSO4) and then concentrated. The residual crystal was recrystallized from ethyl acetate-isopropyl ether to obtain E-2-[4-(5-methyl-2-phenyl-4-oxazolylmethoxy)benzyloxyimino]-2-phenylacetic acid (948 mg, yield 70%) as colorless crystals. m.p. 142-143° C. (decomposition)

Workup

  1. additionwas added
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe ethyl acetate layer was washed with saturated aqueous sodium chloride
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated
  6. customto obtain a colorless oil from a fraction
  7. washeluted with ethyl acetate-hexane (1:2
  8. dissolutionThis oil was dissolved in methanol (5 ml)-1N aqueous solution of sodium hydroxide (5 ml)
  9. temperaturethe mixture was heated
  10. temperatureunder reflux for 3 hours
  11. addition1N HCl (5.5 ml) was added to the reaction mixture
  12. extractionthe mixture was extracted with ethyl acetate
  13. washThe ethyl acetate layer was washed with saturated aqueous sodium chloride
  14. dry with materialdried (MgSO4)
  15. concentrationconcentrated
  16. customThe residual crystal was recrystallized from ethyl acetate-isopropyl ether

Sources & evidence

ORD record
ord-9949d08a6f7d49ba832f183fa5c3550e
Source dataset
uspto-grants-2005_08
Patent number
US06924300B2

Reaction notes

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