Acetic Acid → HCID 14990857, compound

HRID 2248337Notes

Reaction equation

HRID 2248337 reaction equation
[N:1]1([CH2:6][C:7]2[CH:8]=[C:9]([NH:14][C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[C:10]([NH2:13])=[CH:11][CH:12]=2)[CH:5]=[CH:4][N:3]=[CH:2]1.C(O)(=O)C.Cl.[N:26]([O-])=O.[Na+]>O>[N:1]1([CH2:6][C:7]2[CH:12]=[CH:11][C:10]3[N:13]=[N:26][N:14]([C:15]4[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=4)[C:9]=3[CH:8]=2)[CH:5]=[CH:4][N:3]=[CH:2]1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 313Hydrochloric AcidHCID 14990746HCID 14990746, compoundHCID 23668193Sodium Nitrite

Product 1

HCID 14990857HCID 14990857, compoundYield 49%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 1.6 parts of 4-(1H-imidazol-1-ylmethyl)-N2 -phenyl-1,2-benzenediamine, 20 parts of acetic acid and 1.08 parts of concentrated hydrochloric acid was cooled in an ice bath at 12°-16° C. A solution of 0.83 parts of sodium nitrite in 7 parts of water was added dropwise. Upon complete addition, the reaction mixture was allowed to reach room temperature while stirring. The reaction mixture was poured into alkaline ice water and the product was extracted with dichloromethane. The extract was dried, filtered and evaporated. The residue was purified by column chromatography over silica gel first using a mixture of trichloromethane and methanol, saturated with ammonia, (97.5:2.5 by volume) and then a mixture of ethyl acetate, methanol and methanol, saturated with ammonia (95:2.5:2.5 by volume) as eluents. The pure fractions were collected and the eluent was evaporated. The residue was taken up in a mixture of 2-propanone and 2,2'-oxybispropane. The product was filtered off, washed with 2,2'-oxybispropane and dried in vacuo at 60° C., yielding 0.81 parts (49.0%) of 6-(1H-imidazol-1-ylmethyl)-1-phenyl-1H-benzotriazole; mp. 110.1° C. (compound 72).

Workup

  1. temperaturewas cooled in an ice bath at 12°-16° C
  2. additionUpon complete addition
  3. customto reach room temperature
  4. extractionthe product was extracted with dichloromethane
  5. customThe extract was dried
  6. filtrationfiltered
  7. customevaporated
  8. customThe residue was purified by column chromatography over silica gel
  9. additiona mixture of trichloromethane and methanol
  10. additionsaturated with ammonia, (97.5:2.5 by volume) and then a mixture of ethyl acetate, methanol and methanol
  11. customThe pure fractions were collected
  12. customthe eluent was evaporated
  13. additionThe residue was taken up in a mixture of 2-propanone and 2,2'-oxybispropane
  14. filtrationThe product was filtered off
  15. washwashed with 2,2'-oxybispropane
  16. customdried in vacuo at 60° C.

Sources & evidence

ORD record
ord-d850e3239a31487e9d286391bc80784d
Source dataset
uspto-grants-1991_08
Patent number
US05039677

Reaction notes

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