2-Chlorobenzoxazole → HCID 58778601, compound

HRID 1372663Notes

Reaction equation

HRID 1372663 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[C:13]([Cl:24])=[N:14][C:15]([CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20])=[CH:16][CH:17]=1>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[C:13]([Cl:24])=[N:14][C:15]([CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20])=[CH:16][CH:17]=1

Participants

4

Reactant 2

HCID 119862-ChlorobenzoxazoleHCID 72217854HCID 72217854, compound

Product 1

HCID 58778601HCID 58778601, compoundYield 53.5%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

In xylene (100 ml), 2-chlorobenzoxazole (326 μl, 2.86 mmol) and ethyl (3-amino-2-chloro-6-pyridyl)acetate (557 mg, 2.59 mmol) were heated under reflux for 4 hours under stirring. After the reaction mixture was cooled to room temperature, the solvent was distilled off under reduced pressure. The residue was purified by chromatography on a silica gel column, whereby from n-hexane/ethyl acetate (3:1, v/v) eluate fractions, ethyl (3-(2-benzoxazolyl)amino-2-chloro-6-pyridyl)acetate (460 mg, 53%) was obtained as a colorless gum.

Workup

  1. temperatureunder reflux for 4 hours
  2. distillationthe solvent was distilled off under reduced pressure
  3. customThe residue was purified by chromatography on a silica gel column, whereby from n-hexane/ethyl acetate (3:1

Sources & evidence

ORD record
ord-b3fbef928a1c4c88b5d6af301fa34372
Source dataset
uspto-grants-2007_01
Patent number
US07157487B2

Reaction notes

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