p-Toluenesulfonic acid → HCID 136068870, compound

HRID 637461Notes

Reaction equation

HRID 637461 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][C:20]([F:23])=[CH:19][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>[F:23][C:20]1[CH:21]=[CH:22][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:18][CH:19]=1

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 15586657{2-[(3-Aminopyridin-2-yl)amino]phenyl}(4-fluorophenyl)methanone

Product 1

HCID 136068870HCID 136068870, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 11.5 g (0.037 mole) of [2-[(3-amino-2-pyridinyl)amino]phenyl](4-fluorophenyl)methanone and 0.6 g of para toluene sulfonic acid in toluene was refluxed for 24 hr using a Dean-Stark trap to collect water. At the end of reflux, some of the toluene (300 ml) was distilled off and the hot solution was filtered. Pet.-ether (30°-60°) was added to cloud point. The solution was refrigerated overnight (0° C.) and filtered to give 10.7 g crystals. A portion of the material was recrystallized from isopropyl alcohol and dried in vacuo overnight at 65° C., m.p. 203°-205° C.

Workup

  1. temperaturewas refluxed for 24 hr
  2. customto collect water
  3. temperatureAt the end of reflux
  4. distillationsome of the toluene (300 ml) was distilled off
  5. filtrationthe hot solution was filtered
  6. addition-ether (30°-60°) was added to cloud point
  7. filtration(0° C.) and filtered

Sources & evidence

ORD record
ord-2beaaaf039524bc68d325ff97d827a43
Source dataset
uspto-grants-1985_12
Patent number
US04556667

Reaction notes

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