Thionyl Chloride → 1-(2-chloroethyl)-1H-imidazo[4,5-c]quinolin-4-amine

HRID 433167

반응식

HRID 433167 반응식
[NH2:1][C:2]1[C:11]2[N:12]=[CH:13][N:14]([CH2:15][CH2:16]O)[C:10]=2[C:9]2[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=2[N:3]=1.S(Cl)([Cl:20])=O>>[Cl:20][CH2:16][CH2:15][N:14]1[C:10]2[C:9]3[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=3[N:3]=[C:2]([NH2:1])[C:11]=2[N:12]=[CH:13]1

참가 물질

3

반응물 2

HCID 24386Thionyl ChlorideHCID 113566282-(4-amino-1H-imidazo[4,5-c]quinolin-1-yl)ethanol

생성물 1

HCID 223204741-(2-chloroethyl)-1H-imidazo[4,5-c]quinolin-4-amine수율 86%

반응 조건

온도
80 °C

실험 절차

A round bottom flask was charged with a magnetic stir bar, 2-(4-amino-1H-imidazo[4,5-c]quinolin-1-yl)ethanol (8.46 g, 37.06 mmol), and thionyl chloride (68.99 g, 57.99 mmol) under a nitrogen atmosphere. The reaction mixture was heated to 80° C. to give a heterogeneous reaction mixture that was maintained at 80° C. for 2 hours at which time the starting material was completely consumed. The solution was cooled and quenched by the addition of water (400 mL). To the stirred solution was added solid sodium carbonate until the pH reached 10 at which time a solid precipitated out of solution. The solid was collected by filtration to afford 1-(2-chloroethyl)-1H-imidazo[4,5-c]quinolin-4-amine (7.86 g, 31.86 mmol) as an off-white solid. The material was used without further purification.

후처리

  1. additionA round bottom flask was charged with a magnetic stir bar
  2. customto give a heterogeneous reaction mixture that
  3. temperaturewas maintained at 80° C. for 2 hours at which time the starting material
  4. customwas completely consumed
  5. temperatureThe solution was cooled
  6. customquenched by the addition of water (400 mL)
  7. additionTo the stirred solution was added solid sodium carbonate until the pH
  8. customprecipitated out of solution
  9. filtrationThe solid was collected by filtration

출처 및 근거

ORD 기록
ord-c57f447d4e514735a6e2f6d24d7ab561
출처 데이터셋
uspto-grants-2003_12
특허 번호
US06667312B2

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