Benzocaine → Ethyl 4-[(3-methyl-1,2-oxazole-5-carbonyl)amino]benzoate

HRID 2398972Notes

Reaction equation

HRID 2398972 reaction equation
[NH2:1][C:2]1[CH:12]=[CH:11][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:4][CH:3]=1.[CH3:13][C:14]1[CH:18]=[C:17]([C:19](Cl)=[O:20])[O:16][N:15]=1>CC(C)=O>[CH2:9]([O:8][C:6]([C:5]1[CH:4]=[CH:3][C:2]([NH:1][C:19]([C:17]2[O:16][N:15]=[C:14]([CH3:13])[CH:18]=2)=[O:20])=[CH:12][CH:11]=1)=[O:7])[CH3:10]

Participants

4

Reactant 2

HCID 2337BenzocaineHCID 129050993-Methyl-1,2-oxazole-5-carbonyl chloride

Product 1

HCID 16880191Ethyl 4-[(3-methyl-1,2-oxazole-5-carbonyl)amino]benzoateYield 58.4%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a stirred solution of 3.3 g of ethyl p-aminobenzoate in 60 ml of acetone was added 1.46 g of 3-methylisoxazole-5-carbonyl chloride. The mixture was stirred at room temperature for 1 hr. and then refluxed for 1 hr. The solvent was removed and the residue was washed with 5% hydrochloric acid, 5% potassium carbonate and water. Recrystallization from a mixture of benzene and n-hexane gave 1.6 g of pure product. Melting point: 160°-163° C. Yield: 58.4%.

Workup

  1. temperatureand then refluxed for 1 hr
  2. customThe solvent was removed
  3. washthe residue was washed with 5% hydrochloric acid, 5% potassium carbonate and water
  4. customRecrystallization
  5. additionfrom a mixture of benzene and n-hexane

Sources & evidence

ORD record
ord-acee01dfb6944e3584bbc8ae24361d42
Source dataset
uspto-grants-1977_05
Patent number
US04026902

Reaction notes

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