Nitric Acid → HCID 13022631, compound

HRID 1759326Notes

Reaction equation

HRID 1759326 reaction equation
[CH2:1]([N:8]1[C:12]([CH2:13][C:14]([O:16][CH3:17])=[O:15])=[CH:11][N:10]=[C:9]1[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N+:24]([O-])([OH:26])=[O:25].C(=O)(O)[O-].[Na+]>C(O)(=O)C>[N+:24]([C:5]1[CH:4]=[CH:3][C:2]([CH2:1][N:8]2[C:12]([CH2:13][C:14]([O:16][CH3:17])=[O:15])=[CH:11][N:10]=[C:9]2[C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[CH:7][CH:6]=1)([O-:26])=[O:25]

Participants

5

Reactant 3

HCID 944Nitric AcidHCID 516892Sodium BicarbonateHCID 13022630HCID 13022630, compound

Product 1

HCID 13022631HCID 13022631, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

In 20 ml of glacial acetic acid was dissolved 1.2 g of methyl 1-benzyl-2-phenylimidazole-5-acetate, and 20 ml of fuming nitric acid (specific gravity of 1.52) was added to the solution, followed by stirring at room temperature for 2 hours. The reaction solution was poured into 1 l of ice water, neutralized with sodium bicarbonate, and extracted with three 100 ml portions of ethyl acetate. The ethyl acetate layers were combined and evaporated to dryness under reduced pressure, followed by chromatographing on a column of 50 g of silica gel to thereby elute with benzene-ethyl acetate (1:1). The fractions of the objective compound were collected and evaporated to dryness under reduced pressure, yielding 1.25 g of methyl 1-(4-nitrobenzyl)-2-phenylimidazole-5-acetate as colorless crystals. Recrystallization of a part of the compound from benzene-hexane afforded the crystals, m.p. 113°-116° C.

Workup

  1. additionwas added to the solution
  2. extractionextracted with three 100 ml portions of ethyl acetate
  3. customevaporated to dryness under reduced pressure
  4. washto thereby elute with benzene-ethyl acetate (1:1)
  5. customThe fractions of the objective compound were collected
  6. customevaporated to dryness under reduced pressure

Sources & evidence

ORD record
ord-df04e506c5ac4dc89752095cc7c50a83
Source dataset
uspto-grants-1982_07
Patent number
US04340598

Reaction notes

Loading…