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

HRID 2233264
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HRID 2233264 반응식
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
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참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 6344
Dichloromethane
용매

실험 절차

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):

후처리

  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)

출처 및 근거

ORD 기록
ord-66923f15a4fb433f90bfbae4df5881d3
출처 데이터셋
uspto-grants-2010_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07709479B1

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