Nitric Acid → HCID 178519858, compound

HRID 1704188Notes

Reaction equation

HRID 1704188 reaction equation
[C:1]1([C:7]2[NH:8][CH:9]=[C:10]([CH2:12][OH:13])[N:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[N+]([O-])(O)=O.C(=O)([O-])[O-].[Na+].[Na+]>[N+]([O-])(O)=O>[C:1]1([C:7]2[NH:8][CH:9]=[C:10]([CH:12]=[O:13])[N:11]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 944Nitric AcidHCID 10340Sodium CarbonateHCID 10080865(2-Phenyl-1H-imidazol-5-yl)methanol

Product 1

HCID 178519858HCID 178519858, compound

Reagents, catalysts & solvents 1

HCID 944Nitric AcidCatalyst

Conditions

Temperature
0 °C

Procedure

A mixture of 2-phenyl-4-imidazolemethanol (17.4 g) and concentrated nitric acid (13.4 ml) is heated on a steam bath for 2.5hours. Three drops of fuming nitric acid are added to initiate the reaction. Next, the pH is adjusted to 8 with concentrated aqueous sodium carbonate and the mixture is cooled to 0° C overnight. The solid is recovered, washed with water and recrystallized from a mixture of 70 ml of ethyl acetate and 20 ml of petroleum ether giving a yellow solid. Treatment of the mother liquor with petroleum ether gives an additional tacky substance which is triturated with 2-propanol giving a second solid. These two solids are taken up in hot 2-propanol and recrystallized as a yellow solid. This solid is recrystallized from ethanol:water (1:1) yielding yellow crystals, m.p. 169°-171.5° C.

Workup

  1. temperatureis heated on a steam bath for 2.5hours
  2. customthe reaction
  3. customThe solid is recovered
  4. washwashed with water
  5. customrecrystallized from a mixture of 70 ml of ethyl acetate and 20 ml of petroleum ether giving a yellow solid
  6. customTreatment of the mother liquor with petroleum ether gives an additional tacky substance which
  7. customis triturated with 2-propanol giving a second solid
  8. customrecrystallized as a yellow solid
  9. customThis solid is recrystallized from ethanol:water (1:1)
  10. customyielding yellow crystals, m.p. 169°-171.5° C.

Sources & evidence

ORD record
ord-05b1c1f3880848888970672bd7349969
Source dataset
uspto-grants-1978_11
Patent number
US04126444

Reaction notes

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