Hydrogen Bromide → HCID 14518010, compound

HRID 1904827Notes

Reaction equation

HRID 1904827 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][N:9]2[C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=3[N:11]=[C:10]2[S:18][CH:19]2[CH2:24][CH2:23][N:22](S(C3C=CC(C)=CC=3)(=O)=O)[CH2:21][CH2:20]2)=[CH:4][CH:3]=1.Br.C1(O)C=CC=CC=1>O>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][N:9]2[C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=3[N:11]=[C:10]2[S:18][CH:19]2[CH2:20][CH2:21][NH:22][CH2:23][CH2:24]2)=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 260Hydrogen BromideHCID 996PhenolHCID 14013331HCID 14013331, compound

Product 1

HCID 14518010HCID 14518010, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 4.95 parts of 4-[[1-[(4-fluorophenyl)methyl]-1H-benzimidazol-2-yl]thio]-1-[(4-methylphenyl)sulfonyl]piperidine, 225 parts of a hydrobromic acid solution 48% in water and 5 parts of phenol was stirred and refluxed for 2 hours. The reaction mixture was evaporated and the residue as taken up in water and treated with a sodium hydroxide solution. The product was extracted with dichloromethane. The extract was dried, filtered and evaporated. The residue was purified by filtration over silica gel using a mixture of trichloromethane and methanol, saturated with ammonia (95:5 by volume) as eluent. The pure fractions were collected and the eluent was evaporated, yielding 3.4 parts (99%) of 1-[(4-fluorophenyl)methyl]-2-[(4-piperidinyl)thio]-1H-benzimidazole (55).

Workup

  1. temperaturerefluxed for 2 hours
  2. customThe reaction mixture was evaporated
  3. additiontreated with a sodium hydroxide solution
  4. extractionThe product was extracted with dichloromethane
  5. customThe extract was dried
  6. filtrationfiltered
  7. customevaporated
  8. filtrationThe residue was purified by filtration over silica gel using
  9. additiona mixture of trichloromethane and methanol
  10. customThe pure fractions were collected
  11. customthe eluent was evaporated

Sources & evidence

ORD record
ord-d14dd765c9ab429aae9bb3d5f42587c8
Source dataset
uspto-grants-1989_06
Patent number
US04839374

Reaction notes

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