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

HRID 1386258ノート

反応式

HRID 1386258 の反応式
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

参加物

3

反応物 2

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

生成物 1

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

実験手順

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 (×2). 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%).

後処理

  1. temperaturewas heated
  2. temperatureat reflux for 30 minutes
  3. customExcess thionyl chloride was removed by evaporation
  4. customby azeotroping with toluene (×2)
  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

出典と根拠

ORDレコード
ord-637ab674485b4c16aa1783ab67ca896d
出典データセット
uspto-grants-2001_07
特許番号
US06265411B1

反応ノート

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