1,4-Dioxane → 4,5-dichloroimidazole-2-carboxylic acid N-(2-cyanoethyl)-N-methylamide

HRID 1164367Notes

Reaction equation

HRID 1164367 reaction equation
Cl.[CH3:2][NH:3][CH2:4][CH2:5][C:6]#[N:7].[Cl:8][C:9]1[C:13]([Cl:14])=[N:12][C:11](=[C:15](Cl)Cl)[N:10]=1.[O:18]1CCOCC1>>[C:6]([CH2:5][CH2:4][N:3]([CH3:2])[C:15]([C:11]1[NH:12][C:13]([Cl:14])=[C:9]([Cl:8])[N:10]=1)=[O:18])#[N:7]

Participants

4

Reactant 3

HCID 312751,4-DioxaneHCID 124825724,5-Dichloro-2-(dichloromethylidene)-2H-imidazoleHCID 205119223-Methylaminopropionitrile hydrochloride

Product 1

HCID 539822874,5-dichloroimidazole-2-carboxylic acid N-(2-cyanoethyl)-N-methylamideYield 67%

Procedure

24 g (0.2 mol) of 3-methylaminopropionitrile hydrochloride were added to a solution of 21.8 g (0.1 mol) of 4,5-dichloro-2-dichloromethylene-imidazole in 100 ml of dioxane and the mixture was heated to the reflux temperature for two hours, while stirring. After cooling, the product was precipitated with water, filtered off, washed with water and dried. In this way, 16.5 g (67% of theory) of 4,5-dichloroimidazole-2-carboxylic acid N-(2-cyanoethyl)-N-methylamide were obtained. Melting point: 184° C. (from acetonitrile).

Workup

  1. temperaturethe mixture was heated to the reflux temperature for two hours
  2. temperatureAfter cooling
  3. customthe product was precipitated with water
  4. filtrationfiltered off
  5. washwashed with water
  6. customdried

Sources & evidence

ORD record
ord-565c451729094ad8b8df8c8fdbfd1de6
Source dataset
uspto-grants-1983_01
Patent number
US04369186

Reaction notes

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