Trifluoroacetic acid → HCID 178438822, compound

HRID 1723136Notes

Reaction equation

HRID 1723136 reaction equation
[N:1]1([CH:6]([C:9]2[CH:10]=[C:11]([NH2:16])[C:12]([NH2:15])=[CH:13][CH:14]=2)[CH2:7][CH3:8])[CH:5]=[CH:4][N:3]=[CH:2]1.[F:17][C:18]([F:23])([F:22])[C:19](O)=O.[OH-].[NH4+]>>[N:1]1([CH:6]([C:9]2[CH:14]=[CH:13][C:12]3[NH:15][C:19]([C:18]([F:23])([F:22])[F:17])=[N:16][C:11]=3[CH:10]=2)[CH2:7][CH3:8])[CH:5]=[CH:4][N:3]=[CH:2]1

Participants

4

Reactant 3

HCID 6422Trifluoroacetic acidHCID 14923Ammonium HydroxideHCID 20026622HCID 20026622, compound

Product 1

HCID 178438822HCID 178438822, compoundYield 22%

Conditions

Temperature
80 °C

Procedure

A mixture of 6.1 parts of 4-[1-(1H-imidazol-1-yl)propyl]-1,2-benzenediamine and 90 parts of trifluoroacetic acid was stirred for 15 minutes at 80° C. The reaction mixture was poured into crushed ice and treated with ammonium hydroxide. The product was extracted with trichloromethane. The extract was dried, filtered and evaporated. The residue was purified by column chromatography over silica gel using a mixture of trichloromethane, methanol and ammonium hydroxide (90:10:1 by volume) as eluent. The pure fractions were collected and the eluent was evaporated. The residue was crystallized from a mixture of 2-propanone and 2,2'-oxybispropane (4 parts-17.5 parts). The product was filtered off and dried, yielding 1.8 parts (22%) of 5-[1-(1H-imidazol-1-yl)propyl]-2-(trifluoromethyl)-1H-benzimidazole; mp. 173.2° C. (compound 83).

Workup

  1. additionThe reaction mixture was poured
  2. custominto crushed ice
  3. extractionThe product was extracted with trichloromethane
  4. customThe extract was dried
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue was purified by column chromatography over silica gel using
  8. additiona mixture of trichloromethane, methanol and ammonium hydroxide (90:10:1 by volume) as eluent
  9. customThe pure fractions were collected
  10. customthe eluent was evaporated
  11. customThe residue was crystallized from a mixture of 2-propanone and 2,2'-oxybispropane (4 parts-17.5 parts)
  12. filtrationThe product was filtered off
  13. customdried

Sources & evidence

ORD record
ord-bc68fa08c00a4279a76d9bb4d3370f9f
Source dataset
uspto-grants-1989_08
Patent number
US04859684

Reaction notes

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