1,2,4-Trichlorobenzene → 2-hydroxy-N-(2-methylphenyl)benzamide

HRID 433025

Reaction equation

HRID 433025 reaction equation
C1(O)C=CC=CC=1.[C:8]([O:17]C1C=CC=CC=1)(=O)[C:9]1[C:10](=[CH:12][CH:13]=[CH:14][CH:15]=1)[OH:11].[NH2:24][C:25]1[C:26]([CH3:31])=[CH:27][CH:28]=[CH:29][CH:30]=1.ClC1C=CC(Cl)=CC=1Cl>>[CH3:31][C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][C:25]=1[NH:24][C:8](=[O:17])[C:9]1[C:10](=[CH:12][CH:13]=[CH:14][CH:15]=1)[OH:11]

Participants

5

Reactant 4

HCID 131,2,4-TrichlorobenzeneHCID 996PhenolHCID 7242O-ToluidineHCID 8361Phenyl Salicylate

Product 1

HCID 7683182-hydroxy-N-(2-methylphenyl)benzamideYield 90.2%

Procedure

Phenol was distilled from a boiling mixture of phenyl salicylate (42.8 gm, 0.20 mol), 2-toluidine (26.7 gm, 0.25 mol), and 1,2,4-trichlorobenzene (41 mL) as described in the literature procedure (Organic Syntheses, Coll. Vol. 3, 765). The cooled product mixture was transferred to an 250 mL Erlenmeyer flask and boiled with hexanes (75 mL) for 30 minutes. The solid product was isolated from the hot mixture by vacuum filtration. The solid was washed with more hexanes until the filtrate was colorless. Drying gave the pure 2′-methyl-salicylanilide (41 gm, 90%) as an off-white solid.

Workup

  1. customThe solid product was isolated from the hot mixture by vacuum filtration
  2. washThe solid was washed with more hexanes until the filtrate
  3. customDrying

Sources & evidence

ORD record
ord-4da7dd80d24f44b69909143c9a0a173e
Source dataset
uspto-grants-2003_12
Patent number
US06664427B1

Linked notes

Loading…