Oxalyl chloride → 1-Methyl-4-nitro-1H-imidazole-2-carbonyl chloride

HRID 327423Notes

Reaction equation

HRID 327423 reaction equation
[CH3:1][N:2]1[CH:6]=[C:5]([N+:7]([O-:9])=[O:8])[N:4]=[C:3]1[C:10]([OH:12])=O.C(Cl)(=O)C([Cl:16])=O>C1COCC1>[CH3:1][N:2]1[CH:6]=[C:5]([N+:7]([O-:9])=[O:8])[N:4]=[C:3]1[C:10]([Cl:16])=[O:12]

Participants

4

Reactant 2

HCID 65578Oxalyl chlorideHCID 120679981-Methyl-4-nitro-1H-imidazole-2-carboxylic acid

Product 1

HCID 191086291-Methyl-4-nitro-1H-imidazole-2-carbonyl chloride

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1-methyl-4-nitroimidazole-2-carboxylic acid (2.0 g, 0.012 mol) in dry THF (20 mL) was slowly added oxalyl chloride (6 mL). The solution was heated to reflux for 45 minutes, and the solvent and excess oxalyl chloride were removed under reduced pressure to give 1-methyl-4-nitroimidazole-2-carbonyl chloride as a yellow powder which was coevaporated with dry CH2Cl2 (15 mL).

Workup

  1. temperatureThe solution was heated
  2. temperatureto reflux for 45 minutes
  3. customthe solvent and excess oxalyl chloride were removed under reduced pressure

Sources & evidence

ORD record
ord-d05f0e15c49f4f5eaa690a306ce1426a
Source dataset
uspto-grants-1993_12
Patent number
US05273991

Reaction notes

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