Hydrochloric Acid → HCID 14990865, compound

HRID 2248338Notes

Reaction equation

HRID 2248338 reaction equation
[N:1]1([CH2:6][C:7]2[CH:8]=[C:9]([NH:14][CH2:15][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[C:10]([NH2:13])=[CH:11][CH:12]=2)[CH:5]=[CH:4][N:3]=[CH:2]1.Cl.[N:23]([O-])=O.[Na+]>O>[N:1]1([CH2:6][C:7]2[CH:12]=[CH:11][C:10]3[N:13]=[N:23][N:14]([CH2:15][C:16]4[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=4)[C:9]=3[CH:8]=2)[CH:5]=[CH:4][N:3]=[CH:2]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14990747HCID 14990747, compoundHCID 23668193Sodium Nitrite

Product 1

HCID 14990865HCID 14990865, compoundYield 40.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a stirred and cooled (0° C.) mixture of 3.9 parts of 4-(1H-imidazol-1-ylmethyl)-N2 -(phenylmethyl)-1,2-benzenediamine and 9.6 parts of concentrated hydrochloric acid was added dropwise a solution of 1.86 parts of sodium nitrite in 8 parts of water. Upon complete addition, stirring was continued for 10-15 minutes at this low temperature. The reaction mixture was allowed to reach room temperature and poured into ice water. The whole was extracted with dichloromethane. The acid aqueous layer was treated with a concentrated ammonium hydroxide solution while cooling and the product was extracted with dichloromethane. The extract was dried, filtered and evaporated. The residue was purified by filtration over silica gel using a mixture of trichloromethane and methanol (95:5 by volume) as eluent. The pure fractions were collected and the eluent was evaporated. The residue was further purified by column chromatography over silica gel using a mixture of ethyl acetate, methanol and methanol, saturated with ammonia (95:2.5:2.5 by volume) as eluent. The pure fractions were collected and the eluent was evaporated. The product was filtered off, washed with 2,2'-oxybispropane and dried in vacuo at 50° C., yielding 1.6 parts (40.9%) of 6-(1H-imidazol-1-ylmethyl)-1-(phenylmethyl)-1H-benzotriazole; mp. 85.4° C. (compound 80).

Workup

  1. temperaturecooled
  2. additionUpon complete addition
  3. stirringstirring
  4. customto reach room temperature
  5. extractionThe whole was extracted with dichloromethane
  6. additionThe acid aqueous layer was treated with a concentrated ammonium hydroxide solution
  7. temperaturewhile cooling
  8. extractionthe product was extracted with dichloromethane
  9. customThe extract was dried
  10. filtrationfiltered
  11. customevaporated
  12. filtrationThe residue was purified by filtration over silica gel using
  13. additiona mixture of trichloromethane and methanol (95:5 by volume) as eluent
  14. customThe pure fractions were collected
  15. customthe eluent was evaporated
  16. customThe residue was further purified by column chromatography over silica gel using
  17. additiona mixture of ethyl acetate, methanol and methanol
  18. customThe pure fractions were collected
  19. customthe eluent was evaporated
  20. filtrationThe product was filtered off
  21. washwashed with 2,2'-oxybispropane
  22. customdried in vacuo at 50° C.

Sources & evidence

ORD record
ord-2ba51d8a3f2b43b0880cabba1bf0a784
Source dataset
uspto-grants-1991_08
Patent number
US05039677

Reaction notes

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