Methanol → Methyl 2-p-chlorophenyl-5-m-nitrophenoxy-4-oxazoleacetate

HRID 46767Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:9][C:10]([O:17][C:18]3[CH:23]=[CH:22][CH:21]=[C:20]([N+:24]([O-:26])=[O:25])[CH:19]=3)=[C:11]([CH2:13][C:14]([OH:16])=[O:15])[N:12]=2)=[CH:4][CH:3]=1.S(=O)(=O)(O)O.[CH3:32]O>>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:9][C:10]([O:17][C:18]3[CH:23]=[CH:22][CH:21]=[C:20]([N+:24]([O-:26])=[O:25])[CH:19]=3)=[C:11]([CH2:13][C:14]([O:16][CH3:32])=[O:15])[N:12]=2)=[CH:4][CH:3]=1

Participants

Reactant 3

HCID 887Methanol

HCID 1118Sulfuric Acid

HCID 542903892-p-Chlorophenyl-5-m-nitrophenoxy-4-oxazoleacetic acid

Product 1

HCID 54071091Methyl 2-p-chlorophenyl-5-m-nitrophenoxy-4-oxazoleacetate

Procedure

To a solution of 1.0 g of 2-p-chlorophenyl-5-m-nitrophenoxy-4-oxazoleacetic acid in 20 ml of methanol was added 0.02 ml of concentrated sulfuric acid. The mixture was refluxed under heating for 45 minutes on a mantle heater. After the completion of reaction, the solvent was distilled off under reduced pressure. To the residue were added ice-cold water and potassium carbonate, and the mixture was extracted with ethyl acetate. After the organic layer was concentrated, recrystallization of the residue from a mixture of n-hexane and ethyl acetate gave 0.97 g of the title compound, melting at 97°-99° C.

Workup

temperatureThe mixture was refluxed
temperatureunder heating for 45 minutes on a mantle heater
customAfter the completion of reaction
distillationthe solvent was distilled off under reduced pressure
additionTo the residue were added ice-cold water and potassium carbonate
extractionthe mixture was extracted with ethyl acetate
concentrationAfter the organic layer was concentrated
customrecrystallization of the residue
additionfrom a mixture of n-hexane and ethyl acetate

Sources & evidence

ORD record: ord-3621bcf1f2a6409c86b3c15679eae149
Source dataset: uspto-grants-1979_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04175130

Reaction notes

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