Thionyl Chloride → 5-Methyl-4-imidazolecarbonyl chloride hydrochloride

HRID 1719257Notes

Reaction equation

HRID 1719257 reaction equation
[ClH:1].[CH3:2][C:3]1[NH:7][CH:6]=[N:5][C:4]=1[C:8]([OH:10])=O.S(Cl)([Cl:13])=O>CN(C)C=O.C1(C)C=CC=CC=1>[ClH:13].[CH3:2][C:3]1[NH:7][CH:6]=[N:5][C:4]=1[C:8]([Cl:1])=[O:10]

Participants

5

Reactant 2

HCID 24386Thionyl ChlorideHCID 131606155-Methyl-1H-imidazole-4-carboxylic acid hydrochloride (1:1)

Product 1

HCID 202680275-Methyl-4-imidazolecarbonyl chloride hydrochlorideYield 70.1%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

To a suspension of 880 g (5.4 moles) of 5-methyl-4-imidazolecarboxylic acid hydrochloride in 100 ml of dimethylformamide and 2 liters of toluene at 60° C., there was added slowly over 2 hours 790 ml (10.8 moles) of thionyl chloride. At the end of the addition, the mixture was held with good stirring for 1 hour at 80° C. It was allowed to cool, filtered, the solid was washed with 1 liter of toluene. 685 g of 5-methyl-4-imidazolecarbonyl chloride hydrochloride were obtained.

Workup

  1. additionAt the end of the addition
  2. temperatureto cool
  3. filtrationfiltered
  4. washthe solid was washed with 1 liter of toluene

Sources & evidence

ORD record
ord-1508279536a140268bb6e1de6bc96243
Source dataset
uspto-grants-1985_09
Patent number
US04539331

Reaction notes

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