Thionyl Chloride → 4-Chloro-6-methoxy-7-(3-pyrrolidin-1-ylpropoxy)quinazoline

HRID 1791543ノート

反応式

HRID 1791543 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[CH2:22][CH2:21][CH2:20][CH2:19]3)=[C:9]([O:12][CH3:13])[CH:10]=2)[N:5]=[CH:4][N:3]=1.S(Cl)([Cl:25])=O>CN(C=O)C>[Cl:25][C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:14][CH2:15][CH2:16][CH2:17][N:18]3[CH2:22][CH2:21][CH2:20][CH2:19]3)=[C:9]([O:12][CH3:13])[CH:10]=2)[N:5]=[CH:4][N:3]=1

参加物

4

反応物 2

HCID 24386Thionyl ChlorideHCID 178486771HCID 178486771、化合物

生成物 1

HCID 111417924-Chloro-6-methoxy-7-(3-pyrrolidin-1-ylpropoxy)quinazoline

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

A mixture of 4-hydroxy-6-methoxy-7-(3-(pyrrolidin-1-yl)propoxy)quinazoline (1.7 g, 5 mmol) and thionyl chloride (25 ml) containing DMF (0.2 ml) was heated at reflux for 3 hours. Excess thionyl chloride was removed by evaporation and by azeotroping with toluene (×2). The residue was suspended in ether 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 to give 4-chloro-6-methoxy-7-(3-(pyrrolidin-1-yl)propoxy)quinazoline (1.94 g, quantitative).

後処理

  1. temperaturewas heated
  2. temperatureat reflux for 3 hours
  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

出典と根拠

ORDレコード
ord-f0abda1a6a304b70a4c0bcb58c3af872
出典データセット
uspto-grants-2006_07
特許番号
US07074800B1

反応ノート

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