Hydrochloric Acid → HCID 9850511, compound

HRID 2299778Notes

Reaction equation

HRID 2299778 reaction equation
[H-].[Na+].[Br:3][C:4]1[CH:9]=[CH:8][C:7](/[C:10](=[N:16]\[OH:17])/[C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:6][CH:5]=1.Cl[CH2:19][C:20]1[CH:39]=[CH:38][C:23]([O:24][CH2:25][C:26]2[N:27]=[C:28]([C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)[O:29][C:30]=2[CH3:31])=[CH:22][CH:21]=1.Cl.C(=O)(O)[O-].[Na+]>CN(C)C=O>[Br:3][C:4]1[CH:9]=[CH:8][C:7](/[C:10](=[N:16]\[O:17][CH2:19][C:20]2[CH:21]=[CH:22][C:23]([O:24][CH2:25][C:26]3[N:27]=[C:28]([C:32]4[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=4)[O:29][C:30]=3[CH3:31])=[CH:38][CH:39]=2)/[C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:6][CH:5]=1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 516892Sodium BicarbonateHCID 109469404-(4-Chloromethylphenoxy)methyl-5-methyl-2-phenyloxazoleHCID 11022013HCID 11022013, compound

Product 1

HCID 9850511HCID 9850511, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Sodium hydride (60% in oil, 225 mg) was added under a nitrogen atmosphere to a solution of ethyl E-2-(4-bromophenyl)-2-hydroxyiminoacetate (1.73 g) and 4-(4-chloromethylphenoxymethyl)-5-methyl-2-phenyloxazole (2.00 g) in N,N-dimethylformamide (20 ml) at room temperature and the mixture was stirred for 1 hour. After adding 1N HCl (10 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 ethyl E-2-(4-bromophenyl)-2-[4-(5-methyl-2-phenyl-4-oxazolylmethoxy)benzyloxyimino]acetate (2.54 g, yield 73%) as crystals from a fraction eluted with ethyl acetate-hexane (1:3, v/v). Recrystallization was performed from ethyl acetate-hexane. m.p. 105-106° C.

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

Sources & evidence

ORD record
ord-8aa830380f0d4b0b93a116793b64cd3a
Source dataset
uspto-grants-2002_12
Patent number
US06495581B1

Reaction notes

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