p-Toluenesulfonic acid → HCID 135626367, compound

HRID 979614Notes

Reaction equation

HRID 979614 reaction equation
[NH2:1][C:2]1[C:3]([NH:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[C:15]([C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([Cl:23])[CH:18]=2)=O)=[N:4][CH:5]=[CH:6][CH:7]=1.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[Cl:23][C:19]1[CH:18]=[C:17]([C:15]2[C:10]3[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=3[NH:8][C:3]3[N:4]=[CH:5][CH:6]=[CH:7][C:2]=3[N:1]=2)[CH:22]=[CH:21][CH:20]=1

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 15586656{2-[(3-Aminopyridin-2-yl)amino]phenyl}(3-chlorophenyl)methanone

Product 1

HCID 135626367HCID 135626367, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 14 g (0.0433 mole) of [2-[(3-amino-2-pyridinyl)amino]phenyl](3-chlorophenyl)-methanone and 0.3 g of para toluene sulfonic acid in 500 ml of toluene were heated at reflux overnight using a Dean-Stark trap to collect water. At the end of the reflux time, some of the toluene (ca 250 ml) was distilled off and the hot solution was filtered. Pet. ether (30°-60° C.) was added to the cloud point. The solution was refrigerated overnight and filtered to give, after air drying, 10 g (76%) gold colored crystals. A portion was recrystallized from isopropyl alcohol-isopropyl ether, m.p. 160°-160.5° C.

Workup

  1. temperaturewere heated
  2. temperatureat reflux overnight
  3. customto collect water
  4. distillationAt the end of the reflux time, some of the toluene (ca 250 ml) was distilled off
  5. filtrationthe hot solution was filtered
  6. additionPet. ether (30°-60° C.) was added to the cloud point
  7. filtrationfiltered
  8. customto give
  9. customafter air drying
  10. customA portion was recrystallized from isopropyl alcohol-isopropyl ether, m.p. 160°-160.5° C.

Sources & evidence

ORD record
ord-7a9934f6535b4a2a87981549a763cda9
Source dataset
uspto-grants-1987_05
Patent number
US04668675

Reaction notes

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