Hydrochloric Acid → HCID 10178135, compound

HRID 413900Notes

Reaction equation

HRID 413900 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]([C:21](=O)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[CH2:17][C:18](=O)[CH3:19])[CH3:13].[OH-].[Na+].CC1C=CC(S(O)(=O)=O)=CC=1.Cl>C(O)C>[CH2:12]([O:14][C:15]([C:16]1[CH:17]=[C:18]([CH3:19])[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:21]=1[C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1)=[O:29])[CH3:13]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 6101p-Toluenesulfonic acidHCID 84743-Aminobenzenesulfonic acidHCID 14798Sodium HydroxideHCID 14689358Ethyl 2-benzoyl-4-oxopentanoate

Product 1

HCID 10178135HCID 10178135, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Metanilic acid (5 mmol, 0.2 g), 2-benzoyl-4-oxo-pentanoic 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 resulting oil was treated with HCl (hydrochloric acid) at 0° C. to 50° C. to precipitate the unreacted metanilic acid. The remaining material was concentrated under vacuum and purified over silica gel. The named product was collected as brown crystals (m.p. 91° C.-92.5° C.).

Workup

  1. temperatureheated
  2. temperatureunder reflux
  3. customto precipitate the unreacted metanilic acid
  4. concentrationThe remaining material was concentrated under vacuum
  5. custompurified over silica gel
  6. customThe named product was collected as brown crystals (m.p. 91° C.-92.5° C.)

Sources & evidence

ORD record
ord-1f8c75c06df24ecbbe14fe5fb94e9643
Source dataset
uspto-grants-2003_05
Patent number
US06569890B2

Reaction notes

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