p-Toluenesulfonic acid → HCID 9924533, compound

HRID 842207Notes

Reaction equation

HRID 842207 reaction equation
[N+:1]([C:4]1[CH:10]=[CH:9][C:7]([NH2:8])=[CH:6][CH:5]=1)([O-:3])=[O:2].[CH2:11]([O:13][C:14](=[O:28])[CH:15]([C:20](=O)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[CH2:16][C:17](=O)[CH3:18])[CH3:12].CC1C=CC(S(O)(=O)=O)=CC=1>C(O)C>[CH2:11]([O:13][C:14]([C:15]1[CH:16]=[C:17]([CH3:18])[N:8]([C:7]2[CH:9]=[CH:10][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=2)[C:20]=1[C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1)=[O:28])[CH3:12]

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 74754-NitroanilineHCID 14689358Ethyl 2-benzoyl-4-oxopentanoate

Product 1

HCID 9924533HCID 9924533, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

p-Nitroaniline (10 mmol, 1.4 g), 2-benzoyl-4-oxo-pentanoic acid ethyl ester (10 mmol, 2.5 g), and tosic acid (0.1 g) were combined in ethanol, then heated under reflux. The reaction mixture was filtered and the solids washed with ethanol. The collected material was determined to be the named product (m.p. 190° C.-192° C.).

Workup

  1. temperatureheated
  2. temperatureunder reflux
  3. filtrationThe reaction mixture was filtered
  4. washthe solids washed with ethanol

Sources & evidence

ORD record
ord-f7697da638f84ba4b1117be60f6fce43
Source dataset
uspto-grants-2002_04
Patent number
US06372777B1

Reaction notes

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