p-Toluenesulfonic acid monohydrate → HCID 2934792, compound

HRID 842125Notes

Reaction equation

HRID 842125 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:17]=[CH:18][C:19]=1[O:20][CH3:21])[C:6]([NH:8][C:9]1[CH:14]=[C:13]([Cl:15])[CH:12]=[CH:11][C:10]=1[OH:16])=O.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>ClC1C=CC=CC=1Cl.ClCCl>[Cl:15][C:13]1[CH:12]=[CH:11][C:10]2[O:16][C:6]([C:5]3[CH:17]=[CH:18][C:19]([O:20][CH3:21])=[C:3]([O:2][CH3:1])[CH:4]=3)=[N:8][C:9]=2[CH:14]=1

Participants

5

Reactant 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 22618336HCID 22618336, compound

Product 1

HCID 2934792HCID 2934792, compoundYield 31.1%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 72391,2-DichlorobenzeneSolvent

Procedure

A solution of N-(3,4-dimethoxybenzoyl)-2-hydroxy-5-chloroaniline (5.0 g, 0.015 mol) was heated under reflux for 11 hours in 30 ml o-dichlorobenzene and p-toluenesulfonic acid monohydrate (0.3 g, 15 mmol). The reaction mixture was diluted with dichloromethane and filtered through a pad of alumina (25 g). The solvent was evaporated under reduced pressure and the residue was triturated with petroleum ether and filtered to give 2.7 g of crudeproduct. The material was crystallized from methyl t-butyl ether with charcoal to give 1.35 g of material which was crystallized again from methyl t-butyl ether and sublimed at 130° C. (0.05 mm) to give pure title compound as tan crystals, mp 142-145° C.

Workup

  1. filtrationfiltered through a pad of alumina (25 g)
  2. customThe solvent was evaporated under reduced pressure
  3. customthe residue was triturated with petroleum ether
  4. filtrationfiltered
  5. customto give 2.7 g of crudeproduct
  6. customThe material was crystallized from methyl t-butyl ether with charcoal

Sources & evidence

ORD record
ord-dad76459597d44b7b5355d8522cb3ce5
Source dataset
uspto-grants-2002_04
Patent number
US06372770B1

Reaction notes

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