P-Phenylenediamine → N-(4-aminophenyl)-5-methyl-1,2-oxazole-4-carboxamide

HRID 1386826Notes

Reaction equation

HRID 1386826 reaction equation
[CH3:1][C:2]1[O:6][N:5]=[CH:4][C:3]=1[C:7]([OH:9])=O.[CH:10]1[C:15]([NH2:16])=[CH:14][CH:13]=[C:12]([NH2:17])[CH:11]=1.C1(N=C=NC2CCCCC2)CCCCC1>O1CCCC1>[NH2:16][C:15]1[CH:10]=[CH:11][C:12]([NH:17][C:7]([C:3]2[CH:4]=[N:5][O:6][C:2]=2[CH3:1])=[O:9])=[CH:13][CH:14]=1

Participants

5

Reactant 3

HCID 7814P-PhenylenediamineHCID 10868DicyclohexylcarbodiimideHCID 14252405-Methylisoxazole-4-carboxylic acid

Product 1

HCID 10921939N-(4-aminophenyl)-5-methyl-1,2-oxazole-4-carboxamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

10.1 g (0.08 mol) of 5-methylisoxazole-4-carboxylic acid and 8.65 g (0.08 mol) of p-phenylenediamine are dissolved in 300 ml of tetrahydrofuran and 18.05 g (0.088 mol) of dicyclohexylcarbodiimide are added. After 5 hours (“h”), the deposited precipitate is filtered off with suction, the organic phase is concentrated and the product is chromatographed on silica gel by means of ethyl acetate/petroleum ether with addition of 1% glacial acetic acid and then crystallized from ethyl acetate/petroleum ether. The yield of the process was 6.8 g of acetate salt with a melting point of 123° C. to 128° C.

Workup

  1. filtrationthe deposited precipitate is filtered off with suction
  2. concentrationthe organic phase is concentrated
  3. customthe product is chromatographed on silica gel by means of ethyl acetate/petroleum ether with addition of 1% glacial acetic acid
  4. customcrystallized from ethyl acetate/petroleum ether

Sources & evidence

ORD record
ord-61f6eace2daa492cb40b0e25ddf9e17a
Source dataset
uspto-grants-2001_07
Patent number
US06265588B1

Reaction notes

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