Diethylcarbamoyl chloride → HCID 70445405, compound

HRID 746118Notes

Reaction equation

HRID 746118 reaction equation
C(N(CC)CC)C.[CH2:8]([N:10]([CH2:14][CH3:15])[C:11]([Cl:13])=[O:12])[CH3:9].[CH3:16][C:17]1[N:18]=[CH:19][NH:20][C:21]=1[Cl:22]>C(Cl)(Cl)Cl>[ClH:13].[CH2:8]([N:10]([CH2:14][CH3:15])[C:11]([N:20]1[C:21]([Cl:22])=[C:17]([CH3:16])[N:18]=[CH:19]1)=[O:12])[CH3:9]

Participants

5

Reactant 3

HCID 6916Diethylcarbamoyl chlorideHCID 8471TriethylamineHCID 178433268HCID 178433268, compound

Product 1

HCID 70445405HCID 70445405, compoundYield 52.4%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

76 g of triethylamine and, thereafter, 68 g of diethylcarbamyl chloride were added dropwise to 58.5 g of 4-methyl-5-chloroimidazole in 200 ml of chloroform in a stirred flask provided with a thermometer and reflux condenser. Refluxing was then carried out for 2 hours, after which the mixture was cooled and the precipitated triethylamine hydrochloride was filtered off under suction. The filtrate was evaporated down under reduced pressure, 500 ml of acetone was added to the residue, and HCl gas was passed in while the mixture was cooled with ice. The resulting precipitate was filtered off under suction and dried to give 66 g (52.4%) of 1-N-diethylcarbamyl-4-methyl-5-chloroimidazole hydrochloride; mp. from 208° C., with decomposition.

Workup

  1. customprovided with a thermometer
  2. temperaturereflux condenser
  3. temperatureRefluxing
  4. temperatureafter which the mixture was cooled
  5. filtrationthe precipitated triethylamine hydrochloride was filtered off under suction
  6. customThe filtrate was evaporated down under reduced pressure, 500 ml of acetone
  7. additionwas added to the residue, and HCl gas
  8. temperaturewas cooled with ice
  9. filtrationThe resulting precipitate was filtered off under suction
  10. customdried

Sources & evidence

ORD record
ord-0445330a0cbb4524b0d08018809c75d1
Source dataset
uspto-grants-1986_07
Patent number
US04602927

Reaction notes

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