Triethylamine → N-(3-tert-Butyl-1,2-oxazol-5-yl)-2,6-dipropoxybenzamide

HRID 980099Notes

Reaction equation

HRID 980099 reaction equation
[NH2:1][C:2]1[O:6][N:5]=[C:4]([C:7]([CH3:10])([CH3:9])[CH3:8])[CH:3]=1.C(N(CC)CC)C.[CH2:18]([O:21][C:22]1[CH:30]=[CH:29][CH:28]=[C:27]([O:31][CH2:32][CH2:33][CH3:34])[C:23]=1[C:24](Cl)=[O:25])[CH2:19][CH3:20]>O1CCCC1>[CH3:8][C:7]([C:4]1[CH:3]=[C:2]([NH:1][C:24](=[O:25])[C:23]2[C:27]([O:31][CH2:32][CH2:33][CH3:34])=[CH:28][CH:29]=[CH:30][C:22]=2[O:21][CH2:18][CH2:19][CH3:20])[O:6][N:5]=1)([CH3:10])[CH3:9]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 20956943-Tert-butyl-1,2-oxazol-5-amineHCID 132342702,6-Dipropoxybenzoyl chloride

Product 1

HCID 13755289N-(3-tert-Butyl-1,2-oxazol-5-yl)-2,6-dipropoxybenzamideYield 10.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a stirred solution of 2.8 g of 5-amino-3-(1,1-dimethylethyl)isoxazole in 40 ml of tetrahydrofuran containing 4.5 ml of triethylamine was added dropwise over ten minutes a solution of 4.88 g of 2,6-di-n-propoxybenzoyl chloride in 10 ml of tetrahydrofuran. Following the addition, the reaction mixture was heated at reflux for seventy-two hours. The reaction mixture was then cooled to room temperature and the solvent was removed by evaporation under reduced pressure. The residue was dissolved in a mixture of dichloromethane and water, and the organic layer was separated, washed with fresh water, dried, and the solvent was removed by evaporation to provide an oil. The oil was crystallized from Skelly B and diethyl ether to provide 750 mg of N-[3-(1,1-dimethylethyl)-5-isoxazolyl]-2,6-di-n-propoxybenzamide. M.P. 85°-87° C. Yield 10%.

Workup

  1. additionthe addition
  2. temperaturethe reaction mixture was heated
  3. temperatureat reflux for seventy-two hours
  4. customthe solvent was removed by evaporation under reduced pressure
  5. dissolutionThe residue was dissolved in a mixture of dichloromethane and water
  6. customthe organic layer was separated
  7. washwashed with fresh water
  8. customdried
  9. customthe solvent was removed by evaporation
  10. customto provide an oil
  11. customThe oil was crystallized from Skelly B and diethyl ether

Sources & evidence

ORD record
ord-d58336bfdc004d168643661ad8bbf049
Source dataset
uspto-grants-1987_01
Patent number
US04636243

Reaction notes

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