Hydrochloric Acid → HCID 19995903, compound

HRID 2248341Notes

Reaction equation

HRID 2248341 reaction equation
F[C:2]1[CH:7]=[CH:6][C:5]([CH2:8][N:9]2[CH:13]=[CH:12][N:11]=[CH:10]2)=[CH:4][C:3]=1[N+:14]([O-:16])=O.O.[NH2:18][NH2:19].[ClH:20]>C(O)C>[ClH:20].[N:9]1([CH2:8][C:5]2[CH:6]=[CH:7][C:2]3[N:19]=[N:18][N:14]([OH:16])[C:3]=3[CH:4]=2)[CH:13]=[CH:12][N:11]=[CH:10]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 24654Hydrazine hydrate (1:1)HCID 14990940HCID 14990940, compound

Product 1

HCID 19995903HCID 19995903, compoundYield 54.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 6.5 parts of 1-[(4-fluoro-3-nitrophenyl)methyl]-1H-imidazole, 6.01 parts of hydrazine monohydrate and 80 parts of ethanol was stirred and refluxed for 5 hours. After cooling, 12 parts of a hydrochloric acid solution 5N were added. The whole was evaporated. The residue was stirred with 30 parts of water and the precipitated product was filtered off and boiled in 40 parts of 2-propanol. 2-Propanol, saturated with hydrogen chloride, was added. The salt was allowed to crystallize at room temperature. It was filtered off and dried, yielding 4.1 parts (54.3%) of 6-(1H-imidazol-1-ylmethyl)-1H-benzotriazol- 1-ol-monohydrochloride; mp. 207.4° C. (compound 158).

Workup

  1. temperaturerefluxed for 5 hours
  2. temperatureAfter cooling
  3. customThe whole was evaporated
  4. stirringThe residue was stirred with 30 parts of water
  5. filtrationthe precipitated product was filtered off
  6. addition2-Propanol, saturated with hydrogen chloride, was added
  7. customto crystallize at room temperature
  8. filtrationIt was filtered off
  9. customdried

Sources & evidence

ORD record
ord-da79d5942b014286bcf8a4d0a8d02861
Source dataset
uspto-grants-1991_08
Patent number
US05039677

Reaction notes

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