(4-aminophenyl)urea → HCID 178467270, compound

HRID 437974Notes

Reaction equation

HRID 437974 reaction equation
[NH:1]([C:5]1[CH:11]=[CH:10][C:8]([NH2:9])=[CH:7][CH:6]=1)[C:2]([NH2:4])=[O:3].[C:12]([C:15]1[C:16](=[O:26])[O:17][C:18]([OH:25])=[C:19]([C:22](=O)[CH3:23])[C:20]=1[OH:21])(=[O:14])[CH3:13]>CO>[C:12]([C:15]1[C:16](=[O:26])[O:17][C:18](=[O:25])[C:19](=[C:22]([NH:9][C:8]2[CH:10]=[CH:11][C:5]([NH:1][C:2]([NH2:4])=[O:3])=[CH:6][CH:7]=2)[CH3:23])[C:20]=1[OH:21])(=[O:14])[CH3:13]

Participants

4

Reactant 2

HCID 408346(4-aminophenyl)ureaHCID 1354659693,5-Diacetyl-2,6-dihydroxy-4h-pyran-4-one

Product 1

HCID 178467270HCID 178467270, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

A solution of 1.5 g. (0.01 m.) of p-ureidoaniline in 50 ml. of methanol is added to a solution of 2.1 g. (0.01 m.) of 3,5-diacetyl-4,6-dihydroxy 2H-pyran-2-one in 150 ml. of methanol. A solid is formed immediately and the mixture is refluxed for 12 hours. The filtered solid is recrystallized to give 5-acetyl-4-hydroxy-3-[1-(p-ureidophenylamino)ethylidene]-2H-pyran-2,6(3H)-dione, m.p. 250°-253° C.

Workup

  1. customA solid is formed immediately
  2. temperaturethe mixture is refluxed for 12 hours
  3. customThe filtered solid is recrystallized

Sources & evidence

ORD record
ord-fa068a9c58f64ec2ace86ebdae6ef76a
Source dataset
uspto-grants-1977_06
Patent number
US04032652

Reaction notes

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