p-Toluenesulfonic acid → HCID 178428862, compound

HRID 488726Notes

Reaction equation

HRID 488726 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][N:5]=[CH:4][C:3]=1[C:8]1[CH:13]=[CH:12][C:11]([Cl:14])=[CH:10][C:9]=1[Cl:15].C([O:19][CH2:20][CH3:21])(=O)C.[C:22]1(C)C=CC(S(O)(=O)=O)=C[CH:23]=1>C1C=CC=CC=1>[CH3:22][C:23]1[CH:21]=[C:20]([OH:19])[C:7]2[C:2](=[C:3]([C:8]3[CH:13]=[CH:12][C:11]([Cl:14])=[CH:10][C:9]=3[Cl:15])[CH:4]=[N:5][CH:6]=2)[N:1]=1

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 8857Ethyl AcetateHCID 222673263-(2,4-Dichlorophenyl)pyridin-4-amine

Product 1

HCID 178428862HCID 178428862, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A solution of B1 (2.41 g, 10.1 mmole), ethyl acetate (1.31 g, 10.1 mmole) and p-toluenesulfonic acid (70 mg) in benzene (50 ml) is heated at reflux for 2 h. during which 10 ml of solvent is removed by distillation. After evaporation, the residue is added to boiling diphenyl ether (10 ml) and heating is continued for 1 h; then the solution is cooled and poured into high boiling petroleum ether with vigorous stirring. The resulting solid formed is filtered off and washed with diethyl ether to give the product B2.

Workup

  1. customis removed by distillation
  2. customAfter evaporation
  3. additionthe residue is added
  4. temperatureheating
  5. temperaturethen the solution is cooled
  6. additionpoured
  7. customThe resulting solid formed
  8. filtrationis filtered off
  9. washwashed with diethyl ether

Sources & evidence

ORD record
ord-f82d02bce378407597b41adcb05d8c71
Source dataset
uspto-grants-2005_12
Patent number
US06974808B2

Reaction notes

Loading…