Water → 2-(2,3,4,5,6-Pentafluoro-benzylsulfanyl)-1H-benzoimidazole

HRID 1654615Notes

Reaction equation

HRID 1654615 reaction equation
[SH:1][C:2]1[NH:3][C:4]2[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=2[N:6]=1.[OH-].[Na+].[F:13][C:14]1[C:21]([F:22])=[C:20]([F:23])[C:19]([F:24])=[C:18]([F:25])[C:15]=1[CH2:16]Br.O>C(O)C>[F:13][C:14]1[C:21]([F:22])=[C:20]([F:23])[C:19]([F:24])=[C:18]([F:25])[C:15]=1[CH2:16][S:1][C:2]1[NH:3][C:4]2[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=2[N:6]=1

Participants

6

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 74484Pentafluorobenzyl bromideHCID 178527775HCID 178527775, compound

Product 1

HCID 3835052-(2,3,4,5,6-Pentafluoro-benzylsulfanyl)-1H-benzoimidazole

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a slurry of 1.50 g of the 2-mercaptobenzimidazole in 28.5 ml of 95% ethanol was added 0.4 g of sodium hydroxide. After all materials had dissolved, the mixture was added to 2.80 g of 2,3,4,5,6-pentafluorobenzyl bromide. The mixture was stirred at 28°-32° C. for 1 hr, then poured into 150 ml water. The product precipitated, was filtered and dried to yield 2.50 g, mp 189°-196° C. Recrystallization from aqueous methanol yielded 1.95 g, mp 193°-195° C.

Workup

  1. dissolutionAfter all materials had dissolved
  2. customThe product precipitated
  3. filtrationwas filtered
  4. customdried
  5. customto yield 2.50 g, mp 189°-196° C
  6. customRecrystallization from aqueous methanol
  7. customyielded 1.95 g, mp 193°-195° C.

Sources & evidence

ORD record
ord-b206f8f6b93f49aeae89aa63256e4e4e
Source dataset
uspto-grants-1995_04
Patent number
US05409809

Reaction notes

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