4-Fluorobenzoic Acid → HCID 178442514, compound

HRID 1723134Notes

Reaction equation

HRID 1723134 reaction equation
[N:1]1([CH:6]([C:13]2[CH:14]=[C:15]([NH2:20])[C:16]([NH2:19])=[CH:17][CH:18]=2)[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12])[CH:5]=[CH:4][N:3]=[CH:2]1.[F:21][C:22]1[CH:30]=[CH:29][C:25]([C:26](O)=O)=[CH:24][CH:23]=1.[OH-].[NH4+]>>[F:21][C:22]1[CH:30]=[CH:29][C:25]([C:26]2[NH:19][C:16]3[CH:17]=[CH:18][C:13]([CH:6]([N:1]4[CH:5]=[CH:4][N:3]=[CH:2]4)[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12])=[CH:14][C:15]=3[N:20]=2)=[CH:24][CH:23]=1

Participants

4

Reactant 3

HCID 99734-Fluorobenzoic AcidHCID 14923Ammonium HydroxideHCID 14518427HCID 14518427, compound

Product 1

HCID 178442514HCID 178442514, compoundYield 47%

Conditions

Temperature
100 °C

Procedure

A mixture of 9 parts of 4-[1-(1H-imidazol-1-yl)heptyl]-1,2-benzenediamine, 5 parts of 4-fluorobenzoic acid and 100 parts of polyphosphoric acid was stirred for 2 hours at 100° C. After cooling, the reaction mixture was poured into ice water and treated with ammonium hydroxide. The product was extracted three times with 120 parts of trichloromethane. The combined extracts were dried, filtered and evaporated. The residue was purified by column chromatography over silica gel using a mixture of trichloromethane and methanol (98:2 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 1,1'-oxybisethane. The product was filtered off and dried, yielding 5.8 parts (47%) of 2-(4-fluorophenyl)-5-[1-(1H-imidazol-1-yl)heptyl]-1H-benzimidazole; mp. 121.9° C. (compound 39).

Workup

  1. temperatureAfter cooling
  2. extractionThe product was extracted three times with 120 parts of trichloromethane
  3. customThe combined extracts were dried
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue was purified by column chromatography over silica gel using
  7. additiona mixture of trichloromethane and methanol (98:2 by volume) as eluent
  8. customThe pure fractions were collected
  9. customthe eluent was evaporated
  10. customThe residue was crystallized from a mixture of 2-propanone and 1,1'-oxybisethane
  11. filtrationThe product was filtered off
  12. customdried

Sources & evidence

ORD record
ord-bbbdad7c9f964635bc1492db902da15e
Source dataset
uspto-grants-1989_08
Patent number
US04859684

Reaction notes

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