Ammonia → 4,5-Dichloro-2-cyano-imidazole

HRID 2052186Notes

Reaction equation

HRID 2052186 reaction equation
[Cl:1][C:2]1[N:3]=[C:4]([C:8](Cl)(Cl)Cl)[NH:5][C:6]=1[Cl:7].ClC1C(Cl)=NC(=C(Cl)Cl)[N:14]=1.Cl.N>C(O)C>[Cl:1][C:2]1[N:3]=[C:4]([C:8]#[N:14])[NH:5][C:6]=1[Cl:7]

Participants

6

Reactant 4

HCID 222AmmoniaHCID 313Hydrochloric AcidHCID 124825724,5-Dichloro-2-(dichloromethylidene)-2H-imidazoleHCID 124825734,5-Dichloro-2-(trichloromethyl)-1H-imidazole

Product 1

HCID 139615354,5-Dichloro-2-cyano-imidazoleYield 90%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

25.4 g (0.1 mol) of 4,5-dichloro-2-trichloromethyl-imidazole prepared by treating 4,5-dichloro-2-dichloromethylene-imidazole with dry HCl at -20° to +600° C., were introduced in small portions into 200 ml of ethanol saturated with ammonia, whilst cooling with ice and stirring vigorously. The mixture was stirred for a further 30 minutes at 50° C., the constituents which had not dissolved were then filtered off and the filtrate was evaporated under reduced pressure. The combined residues were dissolved in hot water. On acidifying the solution with dilute hydrochloric acid, the reaction product precipited out. This was filtered off, washed with water and dried. In this way 14.6 g (90% of theory) of 4,5-dichloro-2-cyano-imidazole were obtained and after recrystallisation from toluene this had a melting point of 187°-189° C.

Workup

  1. temperaturewhilst cooling with ice
  2. stirringThe mixture was stirred for a further 30 minutes at 50° C.
  3. dissolutionthe constituents which had not dissolved
  4. filtrationwere then filtered off
  5. customthe filtrate was evaporated under reduced pressure
  6. dissolutionThe combined residues were dissolved in hot water
  7. filtrationThis was filtered off
  8. washwashed with water
  9. customdried

Sources & evidence

ORD record
ord-5ca5c466332445ec987c050852df2e73
Source dataset
uspto-grants-1980_01
Patent number
US04183742

Reaction notes

Loading…