Nitric Acid → HCID 178519858, compound

HRID 2419697Notes

Reaction equation

HRID 2419697 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 17.4 gm. portion of 2-phenyl-4-imidazolemethanol and 13.4 ml. of concentrated HNO3 are heated on a steam bath for 21/2 hours. Three drops of fuming HNO3 are added to start the reaction. The pH is adjusted to 8 with concentrated aqueous Na2CO3 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 isopropanol giving a second solid. These two solids are taken up in hot isopropanol and recrystallized as a yellow solid. This solid is recrystallized from ethanol:water (1:1) giving yellow crystals, m.p. 169°-171.5° C.

Workup

  1. customthe reaction
  2. customThe solid is recovered
  3. washwashed with water
  4. customrecrystallized from a mixture of 70 ml
  5. customTreatment of the mother liquor with petroleum ether gives an additional tacky substance which
  6. customis triturated with isopropanol giving a second solid
  7. customrecrystallized as a yellow solid
  8. customThis solid is recrystallized from ethanol:water (1:1)
  9. customgiving yellow crystals, m.p. 169°-171.5° C.

Sources & evidence

ORD record
ord-fba70e642f8e46feb1fcd7f73b6d600d
Source dataset
uspto-grants-1978_08
Patent number
US04107307

Reaction notes

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