1-Methylimidazole → HCID 19000174, compound

HRID 725398Notes

Reaction equation

HRID 725398 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:9]=[C:10]([N+:14]([O-:16])=[O:15])[C:11]=1[O:12][CH3:13])[C:6](Cl)=[O:7].[CH3:17][N:18]1[CH:22]=[CH:21][N:20]=[CH:19]1.C(N(CC)CC)C.[OH-].[Na+]>N1C=CC=CC=1>[CH3:17][N:18]1[CH:22]=[CH:21][N:20]=[C:19]1[C:6]([C:5]1[CH:9]=[C:10]([N+:14]([O-:16])=[O:15])[C:11]([O:12][CH3:13])=[C:3]([O:2][CH3:1])[CH:4]=1)=[O:7]

Participants

6

Reactant 4

HCID 13901-MethylimidazoleHCID 8471TriethylamineHCID 14798Sodium HydroxideHCID 219286153,4-Dimethoxy-5-nitrobenzoyl chloride

Product 1

HCID 19000174HCID 19000174, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent2×

Procedure

A solution of 16.0 g of 3,4-dimethoxy-5-nitrobenzoyl chloride in 80 ml of pyridine is added dropwise to a solution of 2.68 g of 1-methylimidazole and 6.6 g of triethylamine in 80 ml of pyridine, whereupon the mixture is stirred at 60° for 3 hours. After treatment with 1.70 ml of 3N sodium hydroxide solution the mixture is stirred for an additional 1 hour and subsequently poured into ice-water. The separated grey crystals are filtered under suction and taken up in ethyl acetate, whereupon the organic phase is dried over magnesium sulfate and the solvent is distilled. After recrystallization from ethyl acetate/hexane there is obtained 3,4-dimethoxy-5-nitrophenyl (1-methylimidazol-2-yl) ketone in the form of colorless crystals of m.p. 144°-145°.

Workup

  1. filtrationThe separated grey crystals are filtered under suction
  2. dry with materialis dried over magnesium sulfate
  3. distillationthe solvent is distilled
  4. customAfter recrystallization from ethyl acetate/hexane there

Sources & evidence

ORD record
ord-679192bb2f2540c194d1a7eebce25e08
Source dataset
uspto-grants-1998_01
Patent number
US05705703

Reaction notes

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