Water → HCID 17859023, compound

HRID 1372597Notes

Reaction equation

HRID 1372597 reaction equation
Cl[C:2]1[O:3][C:4]2[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=2[N:6]=1.[NH2:11][C:12]1[CH:17]=[CH:16][C:15]([CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20])=[CH:14][CH:13]=1.O>C1(C)C(C)=CC=CC=1>[O:3]1[C:4]2[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=2[N:6]=[C:2]1[NH:11][C:12]1[CH:13]=[CH:14][C:15]([CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20])=[CH:16][CH:17]=1

Participants

5

Reactant 3

HCID 962WaterHCID 119862-ChlorobenzoxazoleHCID 225219p-Aminophenylacetic acid ethyl ester

Product 1

HCID 17859023HCID 17859023, compoundYield 107.8%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

In xylene (10 mL), 2-chlorobenzoxazole (1.00 g, 6.51 mmol) and ethyl 4-aminophenylacetate (1.67 g, 6.51 mmol) were heated and refluxed for 10 hours. After cooling, water was added to the reaction mixture, followed by extraction with ethyl acetate. The extract was washed with saturated brine, dried over magnesium sulfate and distilled under reduced pressure to remove the solvent. The residue was purified by chromatography on a silica gel column, whereby from hexane-ethyl acetate (3:1, v/v) eluate fractions, ethyl 4-(2-benzoxazolylamino)phenylacetate (2.08 g, 99%) was obtained as a yellow solid.

Workup

  1. temperaturerefluxed for 10 hours
  2. temperatureAfter cooling
  3. extractionfollowed by extraction with ethyl acetate
  4. washThe extract was washed with saturated brine
  5. dry with materialdried over magnesium sulfate
  6. distillationdistilled under reduced pressure
  7. customto remove the solvent
  8. customThe residue was purified by chromatography on a silica gel column, whereby from hexane-ethyl acetate (3:1

Sources & evidence

ORD record
ord-26b5d32c22cb40a9a4367ea20b216904
Source dataset
uspto-grants-2007_01
Patent number
US07157487B2

Reaction notes

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