p-Toluenesulfonic acid → HCID 10200089, compound

HRID 842188Notes

Reaction equation

HRID 842188 reaction equation
[CH:1]1[CH:6]=[C:5]([S:7]([OH:10])(=[O:9])=[O:8])[CH:4]=[C:3]([NH2:11])[CH:2]=1.[CH2:12]([O:14][C:15](=[O:29])[CH:16]([CH2:20][C:21](=O)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[C:17](=O)[CH3:18])[CH3:13].[OH-].[Na+].CC1C=CC(S(O)(=O)=O)=CC=1>C(O)C>[CH2:12]([O:14][C:15]([C:16]1[CH:20]=[C:21]([C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=2)[N:11]([C:3]2[CH:2]=[CH:1][CH:6]=[C:5]([S:7]([OH:10])(=[O:8])=[O:9])[CH:4]=2)[C:17]=1[CH3:18])=[O:29])[CH3:13]

Participants

6

Reactant 4

HCID 6101p-Toluenesulfonic acidHCID 84743-Aminobenzenesulfonic acidHCID 14798Sodium HydroxideHCID 312893Ethyl 2-acetyl-4-oxo-4-phenylbutanoate

Product 1

HCID 10200089HCID 10200089, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Metanilic acid (5 mmol, 0.9 g), 3-oxo-2-(2-oxo-2-phenyl-ethyl)-butyric acid ethyl ester (5 mmol, 1.2 g), sodium hydroxide (5 mmol, 0.2 g), and tosic acid (0.1 g) were combined in ethanol, then heated under reflux. The unreacted metanilic acid was precipitated on ice and filtered from the reaction mixture. The filtrate was evaporated to yield an oil, which was purified over silica gel. After standing, the named product solidified as purple crystals (m.p. 94 C.-96° C.).

Workup

  1. temperatureheated
  2. temperatureunder reflux
  3. customThe unreacted metanilic acid was precipitated on ice
  4. filtrationfiltered from the reaction mixture
  5. customThe filtrate was evaporated
  6. customto yield an oil, which
  7. customwas purified over silica gel
  8. customsolidified as purple crystals (m.p. 94 C.-96° C.)

Sources & evidence

ORD record
ord-ba06fed8f91b4d2298c27c3c4acea722
Source dataset
uspto-grants-2002_04
Patent number
US06372777B1

Reaction notes

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