2-Chlorobenzoxazole → Ethyl (4-(2-benzoxazolyl)amino-3-chlorophenyl)acetate

HRID 1372659Notes

Reaction equation

HRID 1372659 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][C:13]=1[Cl:24]>C1(C)C(C)=CC=CC=1.C(Cl)(Cl)Cl>[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:17]=[CH:16][C:15]([CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20])=[CH:14][C:13]=1[Cl:24]

Participants

5

Reactant 2

HCID 119862-ChlorobenzoxazoleHCID 17859298(4-Amino-3-chloro-phenyl)-acetic acid ethyl ester

Product 1

HCID 44606814Ethyl (4-(2-benzoxazolyl)amino-3-chlorophenyl)acetateYield 79%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 7237O-XyleneSolvent

Procedure

In xylene (10 ml), 2-chlorobenzoxazole (743 μl, 6.51 mmol) and ethyl 4-amino-3-chlorophenylacetate (1.30 g, 6.51 mmol) were heated under reflux for 2 hours. After cooling to room temperature, the reaction mixture was diluted with chloroform (50 ml). The mixture was washed with water, 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 (9:1, v/v) eluate fractions, ethyl (4-(2-benzoxazolyl)amino-3-chlorophenyl)acetate (1.70 g, 79%) was obtained as a pale yellow solid.

Workup

  1. temperatureunder reflux for 2 hours
  2. washThe mixture was washed with water
  3. dry with materialdried over anhydrous sodium sulfate
  4. distillationdistilled under reduced pressure
  5. customto remove the solvent
  6. customThe residue was purified by chromatography on a silica gel column, whereby from n-hexane/ethyl acetate (9:1

Sources & evidence

ORD record
ord-9cb8f9a21db647699b4be73efd627eb1
Source dataset
uspto-grants-2007_01
Patent number
US07157487B2

Reaction notes

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