Imidazole → HCID 11790145, compound

HRID 972006Notes

Reaction equation

HRID 972006 reaction equation
[NH:1]1[CH:5]=[CH:4][N:3]=[CH:2]1.CN(C)[CH:8]=[O:9].F[C:12]1[CH:19]=[CH:18][C:15]([C:16]#[N:17])=[CH:14][CH:13]=1.C([O-])([O-])=O.[Na+].[Na+]>C(Cl)(Cl)Cl>[N:1]1([C:8]([C:12]2[CH:19]=[CH:18][C:15]([C:16]#[N:17])=[CH:14][CH:13]=2)=[O:9])[CH:5]=[CH:4][N:3]=[CH:2]1

Participants

6

Reactant 4

HCID 795ImidazoleHCID 6228DimethylformamideHCID 10340Sodium CarbonateHCID 145174-Fluorobenzonitrile

Product 1

HCID 11790145HCID 11790145, compoundYield 48%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
125 °C

Procedure

30 mmoles of [2-14C] imidazole were dissolved in 2.5 ml chloroform and mixed with 18 ml dimethylformamide containing 30.2 mmoles of p-fluorobenzonitrile and 3.2 g Na2CO3. The mixture was stirred at 125° C. for three days [Johnson, J. Med. Chem., Vol. 12, p. 1024 (1969)]. The product was isolated and recrystallized twice from benzene: hexanes (1:1). Yield 48%; mp 152°-154°; elemental analysis: found: 70.85% C, 4.13% H and 24.81% N; theoretical: 70.99% C, 4.17% H and 24.84% N.

Workup

  1. customThe product was isolated
  2. customrecrystallized twice from benzene: hexanes (1:1)

Sources & evidence

ORD record
ord-6e51ee457423476cacbe47029e7aa5f1
Source dataset
uspto-grants-1979_07
Patent number
US04162355

Reaction notes

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