Acetic Acid → HCID 20399521, compound

HRID 1981340Notes

Reaction equation

HRID 1981340 reaction equation
C(N(CC1C=CC=CC=1)[C:9](=[O:35])[CH:10]([C:12]1[CH:17]=[C:16]([CH3:18])[C:15]([N:19]([CH2:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[CH:14][C:13]=1[OH:34])[CH3:11])C1C=CC=CC=1.C(O)(=[O:45])C>Cl>[CH2:27]([N:19]([CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[C:15]1[C:16]([CH3:18])=[CH:17][C:12]([CH:10]([CH3:11])[C:9]([OH:35])=[O:45])=[C:13]([OH:34])[CH:14]=1)[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1

Participants

4

Reactant 2

HCID 176Acetic AcidHCID 13576909HCID 13576909, compound

Product 1

HCID 20399521HCID 20399521, compound

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

20 g of 2-(4-dibenzylamino-2-hydroxy-5-methylphenyl)-propionic acid dibenzylamide are heated under reflux for 3 hours in 40 ml of 2N hydrochloric acid and 40 ml of glacial acetic acid. The mixture is then concentrated to dryness by evaporation in vacuo and the residue is partitioned between ether and 1N sodium hydroxide solution. Acidification to a pH of 1 with hydrochloric acid and extraction yields 2-(4-dibenzylamino-2-hydroxy-5-methylphenyl)-propionic acid which, for purification, is chromatographed over silica gel in methylene chloride. The colourless crystals melt at 174°-175°. 15 g of the crystals are dissolved in 50 ml of ether and 6 g of dicyclohexylcarbodiimide are added thereto. After 30 minutes the urea formed is filtered off and the filtrate is concentrated to dryness by evaporation. In this manner 6-dibenzylamino-3,5-dimethylbenzofuran-2(3H)-one having a melting point of 122°-123° is obtained.

Workup

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

Sources & evidence

ORD record
ord-7290db5db6bd4202b105fbb25133aff9
Source dataset
uspto-grants-1985_04
Patent number
US04514415

Reaction notes

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