Nitric Acid → HCID 178526423, compound

HRID 2248350Notes

Reaction equation

HRID 2248350 reaction equation
[N:1]1([CH2:6][C:7]2[CH:15]=[CH:14][C:10]3[NH:11][N:12]=[N:13][C:9]=3[CH:8]=2)[CH:5]=[CH:4][N:3]=[CH:2]1.[N+:16]([O-])([OH:18])=[O:17]>>[N:1]1([CH2:6][C:7]2[C:15]([N+:16]([O-:18])=[O:17])=[CH:14][C:10]3[NH:11][N:12]=[N:13][C:9]=3[CH:8]=2)[CH:5]=[CH:4][N:3]=[CH:2]1

Participants

3

Reactant 2

HCID 944Nitric AcidHCID 178420758HCID 178420758, compound

Product 1

HCID 178526423HCID 178526423, compoundYield 1.6%

Procedure

2.47 Parts of 5-(1H-imidazol-1-ylmethyl)-1H-benzotriazole were added portionwise to 30 parts of fuming nitric acid while stirring. Upon complete addition, stirring was continued overnight at room temperature. The reaction mixture was poured into 100 parts of crushed ice and nitrogen was bubbled through the mixture during 30 minutes. The precipitated product was filtered off, washed with water and purified by reversed phase chromatography (HPLC) over Li Chroprep RP 18 using a mixture of methanol, acetonitrile and an ammonium acetate solution 0.5% (17:8:75 by volume) as eluent. The desired fraction was collected and the eluent was evaporated. The residue was stirred in methanol and 2,2'-oxybispropane. The precipitated product was filtered off and boiled in methanol. The product was filtered off, washed with methanol and 2,2'-oxybispropane and dried in vacuo at 50°-60° C., yielding 0.05 parts (1.6%) of 5-(1H-imidazol-1-ylmethyl)-6-nitro-1H-benzotriazole; mp. 286.0° C. (decomp.) (compound 235).

Workup

  1. additionUpon complete addition
  2. stirringstirring
  3. additionThe reaction mixture was poured into 100 parts of crushed ice and nitrogen
  4. customwas bubbled through the mixture during 30 minutes
  5. filtrationThe precipitated product was filtered off
  6. washwashed with water
  7. custompurified by reversed phase chromatography (HPLC) over Li Chroprep RP 18 using
  8. additiona mixture of methanol, acetonitrile
  9. customThe desired fraction was collected
  10. customthe eluent was evaporated
  11. stirringThe residue was stirred in methanol
  12. filtrationThe precipitated product was filtered off
  13. filtrationThe product was filtered off
  14. washwashed with methanol and 2,2'-oxybispropane
  15. customdried in vacuo at 50°-60° C.

Sources & evidence

ORD record
ord-e0b010fb51b64c84af76590590c50ee0
Source dataset
uspto-grants-1991_08
Patent number
US05039677

Reaction notes

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