2-Chlorobenzoxazole → HCID 13950999, compound

HRID 1666703Notes

Reaction equation

HRID 1666703 reaction equation
[CH2:1]([O:3][C:4](=[O:7])[CH2:5][OH:6])[CH3:2].[H-].[Na+].Cl[C:11]1[O:12][C:13]2[CH:19]=[CH:18][CH:17]=[CH:16][C:14]=2[N:15]=1>O1CCCC1>[CH2:1]([O:3][C:4](=[O:7])[CH2:5][O:6][C:11]1[O:12][C:13]2[CH:19]=[CH:18][CH:17]=[CH:16][C:14]=2[N:15]=1)[CH3:2]

Participants

5

Reactant 3

HCID 119862-ChlorobenzoxazoleHCID 12184Ethyl GlycolateHCID 24758Sodium hydride

Product 1

HCID 13950999HCID 13950999, compoundYield 86.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

0.14 g (1.3 mmol) ethyl-hydroxyacetate is dissolved in 5 ml tetrahydrofurane and 0.06 g (1.6 mmol) 60% sodium hydride is added to it. After 20 minute stirring 0.16 g (1.1 mmol) 2-chloro-1,3-benzoxazole is added and the mixture is heated under reflux for 3 hours. The solvent is removed, the residue is dissolved in 15 ml water, extracted with 3×20 ml ethyl acetate. The united organic phase is dried over sodium sulfate and evaporated to obtain 0.21 g title compound as an oil. LC-MS[MH+]=222 (C11H11NO4 221.21)

Workup

  1. additionis added
  2. temperaturethe mixture is heated
  3. temperatureunder reflux for 3 hours
  4. customThe solvent is removed
  5. dissolutionthe residue is dissolved in 15 ml water
  6. extractionextracted with 3×20 ml ethyl acetate
  7. dry with materialThe united organic phase is dried over sodium sulfate
  8. customevaporated

Sources & evidence

ORD record
ord-8c401a0262d045a2b8082fbaaa9c7642
Source dataset
uspto-grants-2011_10
Patent number
US08044078B2

Reaction notes

Loading…