2-Chlorobenzoxazole → HCID 12763534, compound

HRID 647246Notes

Reaction equation

HRID 647246 reaction equation
[CH:1]([N:4]([O:9][CH2:10][CH2:11][O:12][CH2:13][CH3:14])[C:5](=[O:8])[CH2:6][OH:7])([CH3:3])[CH3:2].Cl[C:16]1[O:17][C:18]2[CH:24]=[CH:23][CH:22]=[CH:21][C:19]=2[N:20]=1.[OH-].[K+]>C(O)(C)C>[CH:1]([N:4]([O:9][CH2:10][CH2:11][O:12][CH2:13][CH3:14])[C:5](=[O:8])[CH2:6][O:7][C:16]1[O:17][C:18]2[CH:24]=[CH:23][CH:22]=[CH:21][C:19]=2[N:20]=1)([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 119862-ChlorobenzoxazoleHCID 14797Potassium HydroxideHCID 12770729HCID 12770729, compound

Product 1

HCID 12763534HCID 12763534, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

First 20.5 g (0.1 mole) of hydroxyacetic acid N-isopropyl-N-(2-ethoxyethoxy)-amide and then 15.4 g (0.1 mole) of 2-chlorobenzoxazole were added dropwise to a solution of 6.2 g (0.11 mole) of potassium hydroxide in 200 ml of isopropanol at 0° to 5° C., and the mixture was then subsequently stirred for 6 hours, without cooling. The solvent was then distilled off in vacuo, the residue was dissolved in 200 ml of toluene and the solution was extracted by shaking once with 100 ml of water. The organic phase was dried over sodium sulphate and evaporated in vacuo. The residue was subjected to incipient distillation at 60° C. under a high vacuum. 30.3 g (94% of theory) of benzoxazol-2-yl-oxyacetic acid N-isopropyl-N-(2-ethoxy-ethoxy)-amide were obtained in this manner in the form of a light brown oil with a refractive index nD22 of 1.4986.

Workup

  1. temperaturewithout cooling
  2. distillationThe solvent was then distilled off in vacuo
  3. dissolutionthe residue was dissolved in 200 ml of toluene
  4. extractionthe solution was extracted
  5. stirringby shaking once with 100 ml of water
  6. dry with materialThe organic phase was dried over sodium sulphate
  7. customevaporated in vacuo
  8. distillationThe residue was subjected to incipient distillation at 60° C. under a high vacuum

Sources & evidence

ORD record
ord-6164323685534abc85173bac85603538
Source dataset
uspto-grants-1983_10
Patent number
US04408055

Reaction notes

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