Hydrochloric Acid → HCID 178435593, compound

HRID 1723135Notes

Reaction equation

HRID 1723135 reaction equation
[N:1]1([CH:6]([C:8]2[CH:9]=[C:10]([NH2:15])[C:11]([NH2:14])=[CH:12][CH:13]=2)[CH3:7])[CH:5]=[CH:4][N:3]=[CH:2]1.[F:16][C:17]([F:22])([F:21])[C:18](O)=O.Cl>>[N:1]1([CH:6]([C:8]2[CH:13]=[CH:12][C:11]3[NH:14][C:18]([C:17]([F:22])([F:21])[F:16])=[N:15][C:10]=3[CH:9]=2)[CH3:7])[CH:5]=[CH:4][N:3]=[CH:2]1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 6422Trifluoroacetic acidHCID 14518429HCID 14518429, compound

Product 1

HCID 178435593HCID 178435593, compoundYield 69.3%

Procedure

A mixture of 3.6 parts of 4-[1-(1H-imidazol-1-yl)ethyl]-1,2-benzenediamine, 5 parts of trifluoroacetic acid and 100 parts of a hydrochloric acid solution 4N was stirred for 6 hours at reflux temperature. The reaction mixture was concentrated and the concentrate was dissolved in 50 parts of water. The mixture was made alkaline with sodium hydrogen carbonate and the product was extracted with dichloromethane. The extract was dried, filtered and concentrated. The concentrate was purified by column chromatography over silica gel using a mixture of trichloromethane and methanol (97.5:2.5 by volume) as eluent. The pure fractions were collected and the eluent was concentrated. The concentrate was crystallized from 20 parts of ethyl acetate. The product was filtered off and dried, yielding 3.4 parts (69.3%) of 5-[1-(1H-imidazol-1-yl)ethyl]-2-(trifluoromethyl)-1-H-benzimidazole; mp. 164.6° C. (compound 64).

Workup

  1. temperatureat reflux temperature
  2. concentrationThe reaction mixture was concentrated
  3. dissolutionthe concentrate was dissolved in 50 parts of water
  4. extractionthe product was extracted with dichloromethane
  5. customThe extract was dried
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe concentrate was purified by column chromatography over silica gel using
  9. additiona mixture of trichloromethane and methanol (97.5:2.5 by volume) as eluent
  10. customThe pure fractions were collected
  11. concentrationthe eluent was concentrated
  12. customThe concentrate was crystallized from 20 parts of ethyl acetate
  13. filtrationThe product was filtered off
  14. customdried

Sources & evidence

ORD record
ord-ca65af85620f4080abb49087c8120192
Source dataset
uspto-grants-1989_08
Patent number
US04859684

Reaction notes

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