2-Chlorobenzoxazole → Ethyl (4-(2-benzoxazolyl)amino-5-chloro-2-fluorophenyl)acetate

HRID 1372668

Reaction equation

HRID 1372668 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:17]([Cl:18])=[CH:16][C:15]([CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21])=[C:14]([F:25])[CH:13]=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:17]([Cl:18])=[CH:16][C:15]([CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21])=[C:14]([F:25])[CH:13]=1

Participants

4

Reactant 2

HCID 119862-ChlorobenzoxazoleHCID 17858807Ethyl 4-amino-5-chloro-2-fluorophenylacetate

Product 1

HCID 58778947Ethyl (4-(2-benzoxazolyl)amino-5-chloro-2-fluorophenyl)acetateYield 74%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

In xylene (4 ml), 2-chlorobenzoxazole (278 μl, 2.43 mmol) and ethyl (4-amino-5-chloro-2-fluorophenyl)acetate (512 mg, 2.21 mmol) were heated under reflux for 2 hours. After the reaction mixture was cooled to room temperature, the solvent was distilled off under reduced pressure. The residue was dissolved in ethyl acetate. The resulting solution was washed with a saturated aqueous solution of sodium bicarbonate, dried over anhydrous sodium sulfate, and distilled under reduced pressure to remove the solvent. The residue was purified by chromatography on a silica gel column, whereby from n-hexane/ethyl acetate (7:1, v/v) eluate fractions, ethyl (4-(2-benzoxazolyl)amino-5-chloro-2-fluorophenyl)acetate (570 mg, 74%) was obtained as a pale yellow solid.

Workup

  1. temperatureunder reflux for 2 hours
  2. distillationthe solvent was distilled off under reduced pressure
  3. dissolutionThe residue was dissolved in ethyl acetate
  4. washThe resulting solution was washed with a saturated aqueous solution of sodium bicarbonate
  5. dry with materialdried over anhydrous sodium 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 n-hexane/ethyl acetate (7:1

Sources & evidence

ORD record
ord-4f7bd92e4e4c47be9740591b36e80cac
Source dataset
uspto-grants-2007_01
Patent number
US07157487B2

Linked notes

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