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

HRID 432840

反応式

HRID 432840 の反応式
[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

参加物

3

反応物 2

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

生成物 1

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

反応条件

温度
80 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-5f7c5a33f9dd4ef0befc19d36762245b
出典データセット
uspto-grants-2003_12
特許番号
US06664264B2

関連ノート

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