4-Aminobenzoic Acid → 4-[(3-Methyl-1,2-oxazole-5-carbonyl)amino]benzoic acid

HRID 2398971Notes

Reaction equation

HRID 2398971 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[CH3:17][C:18]1[CH:22]=[C:21]([C:23](Cl)=[O:24])[O:20][N:19]=1>CC(C)=O>[C:6]([C:5]1[CH:9]=[CH:10][C:2]([NH:1][C:23]([C:21]2[O:20][N:19]=[C:18]([CH3:17])[CH:22]=2)=[O:24])=[CH:3][CH:4]=1)([OH:8])=[O:7]

Participants

5

Reactant 3

HCID 9784-Aminobenzoic AcidHCID 11430Potassium CarbonateHCID 129050993-Methyl-1,2-oxazole-5-carbonyl chloride

Product 1

HCID 214322274-[(3-Methyl-1,2-oxazole-5-carbonyl)amino]benzoic acidYield 73.7%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a stirred suspension of 6.9g of p-aminobenzoic acid and 3.5 g of potassium carbonate in 60 ml of acetone was added 7.3 g of 3-methylisoxazole-5-carbonyl chloride. The mixture was stirred at room temperature for 1 hr. and then refluxed for 1 hr. The precipitate was filtered off and dissolved in water. The solution was acidified with concentrated hydrochloride acid. The precipitate was filtered off and washed with ethanol. There was obtained 9.1 g of N-(p-carboxyphenyl)-3-methylisoxazole-5-carboxamide. Melting point: above 300° C. Yield: 73.4%.

Workup

  1. temperatureand then refluxed for 1 hr
  2. filtrationThe precipitate was filtered off
  3. dissolutiondissolved in water
  4. filtrationThe precipitate was filtered off
  5. washwashed with ethanol

Sources & evidence

ORD record
ord-3ef31d1a859c46f79597e24cc5a20b64
Source dataset
uspto-grants-1977_05
Patent number
US04026902

Reaction notes

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