p-Toluenesulfonic acid monohydrate → HCID 22618276, compound

HRID 842124Notes

Reaction equation

HRID 842124 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:11][CH2:12][C:13]([NH:15][C:16]2[CH:21]=[C:20]([Cl:22])[CH:19]=[CH:18][C:17]=2[OH:23])=O)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[Cl:22][C:20]1[CH:19]=[CH:18][C:17]2[O:23][C:13]([CH2:12][CH2:11][C:5]3[CH:6]=[CH:7][C:8]([O:9][CH3:10])=[C:3]([O:2][CH3:1])[CH:4]=3)=[N:15][C:16]=2[CH:21]=1

Participants

4

Reactant 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 22618283HCID 22618283, compound

Product 1

HCID 22618276HCID 22618276, compoundYield 64.9%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

N-[3-(3,4-dimethoxyphenyl)propanoyl-2-hydroxy-5-chloro-aniline (2.3 g, 6.3 mmol) in toluene (30 ml) and p-toluenesulfonic acid monohydrate (0.3 g, 1.5 mmol) was heated under reflux for 3 hours. The cooled reaction mixture was decanted from some tar and the toluene was evaporated. The residue was crystallized from t-butyl methyl ether with charcoal to give 1.3 g of the title compound which was recrystallized from t-butyl methyl ether to give pure title compound (1.08 g) mp 102-105° C.

Workup

  1. temperatureunder reflux for 3 hours
  2. customThe cooled reaction mixture
  3. customwas decanted from some tar
  4. customthe toluene was evaporated
  5. customThe residue was crystallized from t-butyl methyl ether with charcoal

Sources & evidence

ORD record
ord-ded5b128ca26463cb4cc01137b729160
Source dataset
uspto-grants-2002_04
Patent number
US06372770B1

Reaction notes

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