Hydrochloric Acid → 4-(Methylthio)-7-(trifluoromethanesulphonyloxy)quinazoline

HRID 2233264Notes

Reaction equation

HRID 2233264 reaction equation
FC(F)(F)S([O:6][S:7]([C:10]([F:13])([F:12])[F:11])(=[O:9])=[O:8])(=O)=O.N1C=CC=C[CH:17]=1.C(O[C:30]1[CH:39]=[C:38]2[C:33]([C:34](=[S:40])[NH:35][CH:36]=[N:37]2)=[CH:32][CH:31]=1)C1C=CC=CC=1.Cl>C(Cl)Cl>[CH3:17][S:40][C:34]1[C:33]2[C:38](=[CH:39][C:30]([O:6][S:7]([C:10]([F:11])([F:12])[F:13])(=[O:8])=[O:9])=[CH:31][CH:32]=2)[N:37]=[CH:36][N:35]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 67749Trifluoromethanesulfonic anhydrideHCID 178527906HCID 178527906, compound

Product 1

HCID 857840454-(Methylthio)-7-(trifluoromethanesulphonyloxy)quinazolineYield 50%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoromethane sulfonic anhydride (0.96 ml, 5.73 mmol) and pyridine (0.46 ml, 5.73 mmol) were added to a solution of 7-benzyloxy-3,4-dihydroquinazolin-4-thione (1.0 g, 5.21 mmol) in methylene chloride (20 ml) at 0° C. for 1.5 hour. Hydrochloric acid (0.5 N) was then added to the mixture which was extracted with ethyl acetate. The organic phase was washed brine, dried over magnesium sulphate and the solvents were removed in vacuo. Purification by flash chromatography on silica gel, eluting with isohexane/ethyl acetate (1:4) yielded 4-(methylthio)-7-(trifluoromethanesulphonyloxy)quinazoline (800 mg, 50% yield):

Workup

  1. extractionwas extracted with ethyl acetate
  2. washThe organic phase was washed brine
  3. dry with materialdried over magnesium sulphate
  4. customthe solvents were removed in vacuo
  5. customPurification by flash chromatography on silica gel
  6. washeluting with isohexane/ethyl acetate (1:4)

Sources & evidence

ORD record
ord-66923f15a4fb433f90bfbae4df5881d3
Source dataset
uspto-grants-2010_05
Patent number
US07709479B1

Reaction notes

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