2-Chlorobenzoxazole → HCID 58778873, compound

HRID 1372661Notes

Reaction equation

HRID 1372661 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][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])=[CH:14][C:13]=1[CH3:26]>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:17]=[CH:16][C:15]([CH2:18][C:19]([O:21][C:22]([CH3:24])([CH3:23])[CH3:25])=[O:20])=[CH:14][C:13]=1[CH3:26]

Participants

4

Reactant 2

HCID 119862-ChlorobenzoxazoleHCID 23512173Tert-butyl 4-amino-3-methylphenylacetate

Product 1

HCID 58778873HCID 58778873, compoundYield 61%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

In xylene (20 ml), 2-chlorobenzoxazole (845 μl, 7.40 mmol) and tert-butyl 4-amino-3-methylphenylacetate (1.26 g, 5.69 mmol) were heated under reflux for 2 hours under stirring. After cooling to room temperature, the reaction mixture was distilled under reduced pressure to remove the solvent. The residue was dissolved in chloroform/methanol (9:1, v/v, 100 ml). The resulting solution 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 (4:1, v/v) eluate fractions, tert-butyl (4-(2-benzoxazolyl)amino-3-methylphenyl)acetate (1.17 g, 61%) was obtained as a yellow amorphous substance.

Workup

  1. temperatureunder reflux for 2 hours
  2. distillationthe reaction mixture was distilled under reduced pressure
  3. customto remove the solvent
  4. dissolutionThe residue was dissolved in chloroform/methanol (9:1, v/v, 100 ml)
  5. washThe resulting solution was washed with water
  6. dry with materialdried over anhydrous sodium sulfate
  7. distillationdistilled under reduced pressure
  8. customto remove the solvent
  9. customThe residue was purified by chromatography on a silica gel column, whereby from n-hexane/ethyl acetate (4:1

Sources & evidence

ORD record
ord-720d20d8f15048cc9455aae468b2f119
Source dataset
uspto-grants-2007_01
Patent number
US07157487B2

Reaction notes

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