p-Toluenesulfonic acid → HCID 9972023, compound

HRID 1090653Notes

Reaction equation

HRID 1090653 reaction equation
C1(C)C=CC(S(O)(=O)=O)=CC=1.O[CH:13]1[S:18][C:17]2=[C:19]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)[C:20](=[O:27])[N:21]([CH2:24][CH2:25][CH3:26])[C:22](=[O:23])[N:16]2[CH2:15][CH2:14]1>C1(C)C=CC=CC=1>[C:28]1([C:19]2[C:20](=[O:27])[N:21]([CH2:24][CH2:25][CH3:26])[C:22](=[O:23])[N:16]3[CH2:15][CH:14]=[CH:13][S:18][C:17]=23)[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=1

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 15027620HCID 15027620, compound

Product 1

HCID 9972023HCID 9972023, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A catalytic amount of p-toluenesulfonic acid was added to a solution of 2-hydroxy-9-phenyl-7-propyl-3,4-dihydro2H,6H-pyrimido[6,1-b][1,3]thiazine-6,8(7H)-dione (0.5 g) in toluene (20 ml) and was refluxed for 5 hours. The reaction solution was concentrated to dryness, and the resulting residue was dissolved in methylene chloride. After washing with water and drying, the solution was concentrated to dryness. The resulting crude crystals were recrystalized from ethyl acetate-isopropyl ether to give colorless prisms (0.33 g, 70%).

Workup

  1. temperaturewas refluxed for 5 hours
  2. concentrationThe reaction solution was concentrated to dryness
  3. dissolutionthe resulting residue was dissolved in methylene chloride
  4. washAfter washing with water
  5. customdrying
  6. concentrationthe solution was concentrated to dryness
  7. customThe resulting crude crystals were recrystalized from ethyl acetate-isopropyl ether

Sources & evidence

ORD record
ord-5329f9c974b141c5bffce8ec818af739
Source dataset
uspto-grants-1992_01
Patent number
US05082838

Reaction notes

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