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

HRID 1791543노트

반응식

HRID 1791543 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[CH2:22][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

참가 물질

4

반응물 2

HCID 24386Thionyl ChlorideHCID 178486771HCID 178486771, 화합물

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-f0abda1a6a304b70a4c0bcb58c3af872
출처 데이터셋
uspto-grants-2006_07
특허 번호
US07074800B1

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