p-Toluenesulfonic acid → HCID 135626376, compound

HRID 543618Notes

Reaction equation

HRID 543618 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]([CH3:23])=[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>[CH3:23][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 15586655HCID 15586655, compound

Product 1

HCID 135626376HCID 135626376, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 3.6 g (0.012 mole) of [2-[(3-amino-2-pyridyl)amino]phenyl](4-methylphenyl)methanone in 100 ml of anhydrous toluene was treated with a catalytic amount of para toluene sulfonic acid and refluxed overnight while separating water with a Dean-Stark trap. The reaction mixture was filtered while hot. The product precipitated as the filtrate cooled to room temperature and was collected by filtration. Weight of solid after solvent evaporated was 2.5 g, m.p. 203.5°-205° C. (decomp.).

Workup

  1. temperaturerefluxed overnight
  2. customwhile separating water with a Dean-Stark trap
  3. filtrationThe reaction mixture was filtered while hot
  4. customThe product precipitated as the filtrate
  5. filtrationwas collected by filtration
  6. customWeight of solid after solvent evaporated

Sources & evidence

ORD record
ord-e7e08cf8a7bb4bb18fdd62e1162c08d6
Source dataset
uspto-grants-1984_05
Patent number
US04447361

Reaction notes

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