Nitric Acid → HCID 178440155, compound

HRID 2419650Notes

Reaction equation

HRID 2419650 reaction equation
[CH2:1]([C:4]1[NH:5][CH:6]=[C:7]([CH2:9][OH:10])[N:8]=1)[CH2:2][CH3:3].[N+]([O-])(O)=O.C([O-])([O-])=O.[Na+].[Na+]>[N+]([O-])(O)=O>[CH2:1]([C:4]1[NH:5][CH:6]=[C:7]([CH:9]=[O:10])[N:8]=1)[CH2:2][CH3:3]

Participants

5

Reactant 3

HCID 944Nitric AcidHCID 10340Sodium CarbonateHCID 178440156HCID 178440156, compound

Product 1

HCID 178440155HCID 178440155, compound

Reagents, catalysts & solvents 1

HCID 944Nitric AcidCatalyst

Conditions

Temperature
0 °C

Procedure

A 108.6 gm. portion of 2-n-propyl-4-imidazolemethanol and 107 ml. of concentrated HNO3 are heated on a steam bath for 2 1/2 hours. Three drops of fuming HNO3 are added during this time. 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 ethyl acetate and petroleum ether giving a yellow solid. Treatment of the mother liquor gives an additional tacky solid 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) giving yellow crystals, m.p. 103.5°-105.5° C.

Workup

  1. customThe solid is recovered
  2. washwashed with water
  3. customrecrystallized from a mixture of ethyl acetate and petroleum ether giving a yellow solid
  4. customTreatment of the mother liquor gives an additional tacky solid which
  5. customis triturated with 2-propanol giving a second solid
  6. customrecrystallized as a yellow solid
  7. customThis solid is recrystallized from ethanol:water (1:1)
  8. customgiving yellow crystals, m.p. 103.5°-105.5° C.

Sources & evidence

ORD record
ord-6bdce8b94752439f9415eb86ac5d2806
Source dataset
uspto-grants-1978_08
Patent number
US04107308

Reaction notes

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