Sodium benzenethiolate → 1-[2-(phenylthio)ethyl]-1H-imidazo[4,5-c]quinolin-4-amine

HRID 432841

反応式

HRID 432841 の反応式
Cl[CH2:2][CH2:3][N:4]1[C:16]2[C:15]3[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=3[N:9]=[C:8]([NH2:17])[C:7]=2[N:6]=[CH:5]1.[C:18]1([S-:24])[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.[Na+]>CS(C)=O>[C:18]1([S:24][CH2:2][CH2:3][N:4]2[C:16]3[C:15]4[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=4[N:9]=[C:8]([NH2:17])[C:7]=3[N:6]=[CH:5]2)[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

参加物

4

反応物 2

HCID 4110039Sodium benzenethiolateHCID 223204741-(2-chloroethyl)-1H-imidazo[4,5-c]quinolin-4-amine

生成物 1

HCID 98582651-[2-(phenylthio)ethyl]-1H-imidazo[4,5-c]quinolin-4-amine収率 80%

試薬・触媒・溶媒 1

HCID 679Dimethyl Sulfoxide溶媒

反応条件

温度
100 °C

実験手順

A round bottom flask was charged with a magnetic stir bar, 1-(2-chloroethyl)-1H-imidazo[4,5-c]quinolin-4-amine (2.0 g, 8.11 mmol), sodium benzenethiolate (1.79 g, 12.16 mmol), and anhydrous dimethyl sulfoxide (40 mL) under a nitrogen atmosphere. The reaction mixture was heated to 100° C. to give a homogeneous solution that was maintained at 100° C. for 30 minutes at which time the starting material was completely consumed. The hot solution was poured into rapidly stirred water (300 mL) which caused a solid to precipitate out of solution. The solid was collected by filtration to afford an off-white solid. The material was triturated with acetonitrile and collected by filtration to give 1-[2-(phenylthio)ethyl]-1H-imidazo[4,5-c]quinolin-4-amine (2.08 g, 6.49 mmol) as an off-white powder, m. p. 233-235° C.

後処理

  1. additionA round bottom flask was charged with a magnetic stir bar
  2. customto give a homogeneous solution that
  3. temperaturewas maintained at 100° C. for 30 minutes at which time the starting material
  4. customwas completely consumed
  5. additionThe hot solution was poured into rapidly stirred water (300 mL) which
  6. customto precipitate out of solution
  7. filtrationThe solid was collected by filtration
  8. customto afford an off-white solid
  9. customThe material was triturated with acetonitrile
  10. filtrationcollected by filtration

出典と根拠

ORDレコード
ord-1565fd21000840d2bdf5e930a6ab094c
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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