Thionyl Chloride → 4-Chloro-6-methoxy-7-(3-morpholin-4-ylpropoxy)quinazoline

HRID 855678노트

반응식

HRID 855678 반응식
O[C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:14][CH2:15][CH2:16][CH2:17][N:18]3[CH2:23][CH2:22][O:21][CH2:20][CH2:19]3)=[C:9]([O:12][CH3:13])[CH:10]=2)[N:5]=[CH:4][N:3]=1.S(Cl)([Cl:26])=O>>[Cl:26][C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:14][CH2:15][CH2:16][CH2:17][N:18]3[CH2:23][CH2:22][O:21][CH2:20][CH2:19]3)=[C:9]([O:12][CH3:13])[CH:10]=2)[N:5]=[CH:4][N:3]=1

참가 물질

3

반응물 2

HCID 24386Thionyl ChlorideHCID 1784867726-methoxy-7-(3-morpholin-4-ylpropoxy)-1H-quinazolin-4-one

생성물 1

HCID 118239414-Chloro-6-methoxy-7-(3-morpholin-4-ylpropoxy)quinazoline수율 87%

실험 절차

A mixture of 4-hydroxy-6-methoxy-7-(3-morpholinopropoxy)quinazoline (638 mg, 2 mmol) and thionyl chloride (8 ml) was heated at reflux for 30 minutes. Excess thionyl chloride was removed by evaporation and by azeotroping with toluene (x2). The residue was suspended in methylene chloride and 10% aqueous solution of sodium hydrogen carbonate was added to the mixture. The organic layer was separated, dried (MgSO4) and the solvent removed by evaporation. The residue was triturated with ether, the solid was collected by filtration, washed with ether and dried under vacuum to give 4-chloro-6-methoxy-7-(3-morpholinopropoxy)quinazoline (590 mg, 87%).

후처리

  1. temperaturewas heated
  2. temperatureat reflux for 30 minutes
  3. customExcess thionyl chloride was removed by evaporation
  4. customby azeotroping with toluene (x2)
  5. addition10% aqueous solution of sodium hydrogen carbonate was added to the mixture
  6. customThe organic layer was separated
  7. dry with materialdried (MgSO4)
  8. customthe solvent removed by evaporation
  9. customThe residue was triturated with ether
  10. filtrationthe solid was collected by filtration
  11. washwashed with ether
  12. customdried under vacuum

출처 및 근거

ORD 기록
ord-97558b8b7a464a3788f102ecbfc548a2
출처 데이터셋
uspto-grants-2007_08
특허 번호
US07262201B1

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