1-Methylimidazole → HCID 19000174, compound

HRID 274530Notes

Reaction equation

HRID 274530 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-7c123fa4b1664102a0e23bfb500571d7
Source dataset
uspto-grants-1995_02
Patent number
US05389653

Reaction notes

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