HCID 70478937, compound → HCID 20399521, compound

HRID 544731Notes

Reaction equation

HRID 544731 reaction equation
C1C(C(NC(C2C=CC=CC=2)=O)=O)=CC=CC=1.[CH2:18]([N:25]([CH2:39][C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1)[C:26]1[C:31]([CH3:32])=[CH:30][C:29]([CH:33]([CH3:37])[C:34]([OH:36])=[O:35])=[C:28]([OH:38])[CH:27]=1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>Cl.C(O)(=O)C>[CH2:39]([N:25]([CH2:18][C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1)[C:26]1[C:31]([CH3:32])=[CH:30][C:29]([CH:33]([CH3:37])[C:34]([OH:36])=[O:35])=[C:28]([OH:38])[CH:27]=1)[C:40]1[CH:41]=[CH:42][CH:43]=[CH:44][CH:45]=1

Participants

4

Reactant 1

HCID 70478937HCID 70478937, compound

Product 1

HCID 20399521HCID 20399521, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 313Hydrochloric AcidSolvent

Procedure

20 g of 2-(4-dibenzylamino-2-hydroxy-5-methylphenyl)-propionic acid dibenzamide are heated under reflux for 3 hours in 40 ml of 2 N hydrochloric acid and 40 ml of glacial acetic acid. Subsequently, the mixture is concentrated to dryness by evaporation in vacuo and the residue is partitioned between ether and 1 N sodium hydroxide solution. Acidification to a pH of 1 with hydrochloric acid and extraction with ether yields 2-[4-dibenzylamino-2-hydroxy-5-methylphenyl]-propionic acid, which for purification is chromatographed over silica gel with methylene chloride. The colourless crystals melt at 174°-175° C. 5 g of the crystals are dissolved in 50 ml of ether and 6 g of dicyclohexylcarbodiimide are added. After 30 minutes, the urea that has formed is filtered off and the filtrate is concentrated to dryness by evaporation. In this manner 6-dibenzylamino-3,5-dimethyl-benzofuran-2(3H)-one having a melting point of 122°-123° C. is obtained.

Workup

  1. concentrationSubsequently, the mixture is concentrated to dryness by evaporation in vacuo
  2. customthe residue is partitioned between ether and 1 N sodium hydroxide solution
  3. extractionAcidification to a pH of 1 with hydrochloric acid and extraction with ether

Sources & evidence

ORD record
ord-acc9673bde01404f99861ab4a35386d3
Source dataset
uspto-grants-1984_05
Patent number
US04451462

Reaction notes

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