p-Toluenesulfonic acid → HCID 178431394, compound

HRID 231141Notes

Reaction equation

HRID 231141 reaction equation
[OH:1][CH:2]([C:5]1[C:14]([C:15]([NH:17][C:18]2[S:19][CH:20]=[CH:21][N:22]=2)=[O:16])=[C:13]([OH:23])[C:12]2[C:7](=[C:8]([C:24]([F:27])([F:26])[F:25])[CH:9]=[CH:10][CH:11]=2)[N:6]=1)[CH2:3][OH:4].[C:28]1(C)[CH:33]=CC(S(O)(=O)=O)=C[CH:29]=1>CC(C)=O>[CH3:29][C:28]1([CH3:33])[O:1][CH:2]([C:5]2[C:14]([C:15]([NH:17][C:18]3[S:19][CH:20]=[CH:21][N:22]=3)=[O:16])=[C:13]([OH:23])[C:12]3[C:7](=[C:8]([C:24]([F:26])([F:25])[F:27])[CH:9]=[CH:10][CH:11]=3)[N:6]=2)[CH2:3][O:4]1

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 178522558HCID 178522558, compound

Product 1

HCID 178431394HCID 178431394, compoundYield 156.8%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
20 °C

Procedure

A suspension of 3 g of the product of Example 2 in 80 ml of acetone was heated to reflux and 0.3 g of p-toluene sulfonic acid were added. The mixture was refluxed for 5 hours, was cooled to 20° C. and was vacuum filtered. The crystals were dried under reduced pressure and dissolved in 100 ml of tetrahydrofuran warmed to 40° C. The mixture was filtered and was concentrated to one half volume. The mixture was cooled to 20° C. and ether was added. The mixture was vacuum filtered and the crystals were washed with ether and dried to obtain 1.2 g of 2-(2,2-dimethyl-1,3-dioxolan-4-yl)-4-hydroxy-N-(2-thiazolyl)-8-trifluoromethyl-3-quinoline-carboxamide melting at 250° C.

Workup

  1. temperaturewas heated
  2. temperatureto reflux
  3. temperatureThe mixture was refluxed for 5 hours
  4. filtrationfiltered
  5. customThe crystals were dried under reduced pressure
  6. dissolutiondissolved in 100 ml of tetrahydrofuran
  7. temperaturewarmed to 40° C
  8. filtrationThe mixture was filtered
  9. concentrationwas concentrated to one half volume
  10. temperatureThe mixture was cooled to 20° C.
  11. additionether was added
  12. filtrationfiltered
  13. washthe crystals were washed with ether
  14. customdried

Sources & evidence

ORD record
ord-028d6fdd498e4e4b932db908429a542d
Source dataset
uspto-grants-1989_07
Patent number
US04845105

Reaction notes

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