p-Toluenesulfonic acid → HCID 15027679, compound

HRID 1090655Notes

Reaction equation

HRID 1090655 reaction equation
[C:1]1([C:7]2[C:8](=[O:18])[NH:9][C:10](=[O:17])[N:11]3[CH2:16][CH:15]=[CH:14][S:13][C:12]=23)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:19][C:20]1[CH:27]=[CH:26][C:23]([CH2:24]Cl)=[CH:22][CH:21]=1.C(=O)([O-])[O-].[K+].[K+].C1(C)C=CC(S(O)(=O)=O)=CC=1>CN(C=O)C.C1(C)C=CC=CC=1>[CH3:19][C:20]1[CH:27]=[CH:26][C:23]([CH2:24][N:9]2[C:8](=[O:18])[C:7]([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)=[C:12]3[S:13][CH:14]=[CH:15][CH2:16][N:11]3[C:10]2=[O:17])=[CH:22][CH:21]=1

Participants

7

Reactant 4

HCID 6101p-Toluenesulfonic acidHCID 77224-Methylbenzyl chlorideHCID 11430Potassium CarbonateHCID 15027677HCID 15027677, compound

Product 1

HCID 15027679HCID 15027679, compoundYield 33%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 9-phenyl-4H,6H-pyrimido[6,1-b][1,3]thiazine-6,8(7H)-dione (0.26 g), p-methylbenzylchloride (0.21 g) and potassium carbonate (0.28 g) in DMF (5 ml) was stirred at 100° C. for 15 hours. The reaction solution was concentrated to dryness. The resulting residue was dissolved in dichloroethane and was washed with water and dried. m-Chloroperbenzoic acid (0.2 g) was added to the dichloroethane solution little by little under ice cooling, and it was allowed to stand at room temperature for 15 hours. The reaction solution was washed with saturated aq. sodium bicarbonate, and dried, and then trifluoro acetic acid anhydride (0.5 ml) was added thereto and the mixture was refluxed for 15 hours. Oily product obtained by concentration of the resulting solution was dissolved in toluene (20 ml), and a catalytic amount of p-toluene sulfonic acid was added thereto and the mixture was refluxed for 10 hours. The reaction solution was washed with sodium bicarbonate and water, followed by concentration to dryness. The obtained crude crystals were recrystallized from ethyl ether to give colorless crystals (0.12 g, 33%).

Workup

  1. concentrationThe reaction solution was concentrated to dryness
  2. dissolutionThe resulting residue was dissolved in dichloroethane
  3. washwas washed with water
  4. customdried
  5. additionm-Chloroperbenzoic acid (0.2 g) was added to the dichloroethane solution little by little under ice cooling, and it
  6. waitto stand at room temperature for 15 hours
  7. washThe reaction solution was washed with saturated aq. sodium bicarbonate
  8. customdried
  9. additiontrifluoro acetic acid anhydride (0.5 ml) was added
  10. temperaturethe mixture was refluxed for 15 hours
  11. customOily product obtained by concentration of the resulting solution
  12. temperaturethe mixture was refluxed for 10 hours
  13. washThe reaction solution was washed with sodium bicarbonate and water
  14. concentrationfollowed by concentration to dryness
  15. customThe obtained crude crystals
  16. customwere recrystallized from ethyl ether

Sources & evidence

ORD record
ord-042842ee2ad04055855d5d0889115d79
Source dataset
uspto-grants-1992_01
Patent number
US05082838

Reaction notes

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