Oxalyl chloride → 5-methyl-1H-imidazole-4-carboxylic acid chloride

HRID 1285223Notes

Reaction equation

HRID 1285223 reaction equation
[CH3:1][C:2]1[NH:6][CH:5]=[N:4][C:3]=1[C:7]([OH:9])=O.C(Cl)(=O)C([Cl:13])=O>CN(C)C=O.O1CCCC1.C(OCC)C>[CH3:1][C:2]1[NH:6][CH:5]=[N:4][C:3]=1[C:7]([Cl:13])=[O:9]

Participants

6

Reactant 2

HCID 65578Oxalyl chlorideHCID 738254-Methyl-1H-imidazole-5-carboxylic acid

Product 1

HCID 202680235-methyl-1H-imidazole-4-carboxylic acid chloride

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideCatalystHCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

Under a dry nitrogen atmosphere, a stirred suspension of 5-methyl-1H-imidazole-4-carboxylic acid (12.6 g, 0.10 mole) and several drops of dimethylformamide in 125 ml of dry tetrahydrofuran was cooled in an ice bath. Oxalyl chloride, 20 ml, in 50 ml of tetrahydrofuran was carefully added dropwise. Upon complete addition the reaction mixture was heated under reflux for two hours, cooled to ambient temperature and diluted with 100 ml of diethyl ether. A solid precipitated and was collected by filtration, washed with diethyl ether, and dried to give 5-methyl-1H-imidazole-4-carboxylic acid chloride.

Workup

  1. temperaturewas cooled in an ice bath
  2. additionUpon complete addition the reaction mixture
  3. temperaturewas heated
  4. temperatureunder reflux for two hours
  5. customA solid precipitated
  6. filtrationwas collected by filtration
  7. washwashed with diethyl ether
  8. customdried

Sources & evidence

ORD record
ord-9aa02993ea254502a5c38584eeeb7123
Source dataset
uspto-grants-1986_01
Patent number
US04565875

Reaction notes

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