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

HRID 327427Notes

Reaction equation

HRID 327427 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 chloride2×HCID 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 8028TetrahydrofuranSolvent2×

Procedure

To a suspension of 1-methyl-4-nitroimidazole-2-carboxylic acid (3.00 g, 17.5 mmol) in dry THF (30 mL) was slowly added oxalyl chloride (12 mL). The reaction mixture was heated to reflux under a drying tube for 45 minutes at which time the excess oxalyl chloride and THF were removed under reduced pressure and the acid chloride coevaporated twice with dry CH2Cl2 (20 mL each) yielding 1-methyl-4-nitroimidazole-2-carbonyl chloride as a yellow powder.

Workup

  1. temperatureThe reaction mixture was heated
  2. customwere removed under reduced pressure

Sources & evidence

ORD record
ord-c4c400ae5f8048268425aac0e1979e00
Source dataset
uspto-grants-1993_12
Patent number
US05273991

Reaction notes

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