Water → HCID 12947398, compound

HRID 2052532

Reaction equation

[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

Participants

Conditions

Temperature: 60 °C

Procedure

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.

Workup

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

Sources & evidence

ORD record: ord-35d6ab11edad4e91b4c6ae572768eda3
Source dataset: uspto-grants-1980_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04185992

Linked notes

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