Water → 1-(3,4-Dichlorobenzyl)-4,5-dicyanoimidazole

HRID 2052532

反応式

HRID 2052532 の反応式
[C:1]([C:3]1[N:4]=[CH:5][NH:6][C:7]=1[C:8]#[N:9])#[N:2].[H-].[Na+].[Cl:12][C:13]1[CH:14]=[C:15]([CH:18]=[CH:19][C:20]=1[Cl:21])[CH2:16]Cl.O>CN(C)C=O>[Cl:12][C:13]1[CH:14]=[C:15]([CH:18]=[CH:19][C:20]=1[Cl:21])[CH2:16][N:4]1[C:3]([C:1]#[N:2])=[C:7]([C:8]#[N:9])[N:6]=[CH:5]1

参加物

6

反応物 4

HCID 962WaterHCID 76093,4-Dichlorobenzyl chlorideHCID 24758Sodium hydrideHCID 707294,5-Dicyanoimidazole

生成物 1

HCID 129473981-(3,4-Dichlorobenzyl)-4,5-dicyanoimidazole

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
60 °C

実験手順

4,5-Dicyanoimidazole (93 g, described by Woodward, U.S. Pat. No. 2534331 (1950)) was dissolved in dry dimethylformamide (500 ml) with stirring. Sodium hydride (20 g) was added to the solution in portions at such a rate that the temperature after the addition was 90° C. When effervescence had ceased the solution was heated on a steam bath for 15 minutes and then allowed to cool to 60° C. 3,4-Dichlorobenzyl chloride (230 g, described by Beilstein & Kuhlberg, Ann., 146, 326 (1867)) was added over 30 minutes to the solution, which was heated on a steam bath for 6 hours and then at 150° C. for 10 minutes. The cooled reaction mixture was poured into water (2 liters) and a brown solid was filtered off and washed with water. The damp solid was recrystallised from ethanol (1 liter) to give 1-(3,4-dichlorobenzyl)-4,5-dicyanoimidazole, m.p. 132°-134° C., (114 g) as off-white crystals.

後処理

  1. additionafter the addition
  2. customwas 90° C
  3. temperaturewas heated on a steam bath for 15 minutes
  4. temperaturewas heated on a steam bath for 6 hours
  5. customThe cooled reaction mixture
  6. filtrationa brown solid was filtered off
  7. washwashed with water
  8. customThe damp solid was recrystallised from ethanol (1 liter)

出典と根拠

ORDレコード
ord-35d6ab11edad4e91b4c6ae572768eda3
出典データセット
uspto-grants-1980_01
特許番号
US04185992

関連ノート

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