Hydrochloric Acid → 5-(4-fluorophenyl)-2-hydroxymethyl-4-(4-methylthiophenyl)-1H-imidazole

HRID 53844Notes

Reaction equation

HRID 53844 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[NH:12][C:11]([CH:13]=[O:14])=[N:10][C:9]=2[C:15]2[CH:20]=[CH:19][C:18]([S:21][CH3:22])=[CH:17][CH:16]=2)=[CH:4][CH:3]=1.[BH4-].[Na+].Cl.C([O-])(O)=O.[Na+]>CO>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[NH:12][C:11]([CH2:13][OH:14])=[N:10][C:9]=2[C:15]2[CH:20]=[CH:19][C:18]([S:21][CH3:22])=[CH:17][CH:16]=2)=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 4311764Sodium borohydrideHCID 540330095-(4-fluorophenyl)4-(4-methylthiophenyl)-1H-imidazole-2-carboxaldehyde

Product 1

HCID 536747975-(4-fluorophenyl)-2-hydroxymethyl-4-(4-methylthiophenyl)-1H-imidazoleYield 78%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of compound from step 3 (350 mg, 1 mmol) and NaBH4 (75 mg, 2 eg.) in methanol (10 ml) was stirred for 1 hour at 25° C. The reaction was acidified with 2N HCl (4 ml), stirred for 2 hours and placed on a steam bath for 2 minutes. After cooling, the mixture was neutralized with aqueous NaHCO3 solution, extracted with methylene chloride, dried (MgSO4) and evaporated. The residue was chromatographed on silica gel, eluting with toluene/methanol (90/10). The crude product was recrystallized from ethyl acetate/hexane to give 240 mg (78%) of pure 5-(4-fluorophenyl)-2-hydroxymethyl-4-(4-methylthiophenyl)-1H-imidazole: m.p. 108°-110° C. Anal. Calc'd. for C17H15N20FS: C, 64.95; H, 4.81; N, 8.91; S, 10.20. Found: C, 64.69; H, 4.92; N, 8.79; S, 10.41.

Workup

  1. waitplaced on a steam bath for 2 minutes
  2. temperatureAfter cooling
  3. extractionextracted with methylene chloride
  4. dry with materialdried (MgSO4)
  5. customevaporated
  6. customThe residue was chromatographed on silica gel
  7. washeluting with toluene/methanol (90/10)
  8. customThe crude product was recrystallized from ethyl acetate/hexane

Sources & evidence

ORD record
ord-c5c5bcd64058426086b5d1a7c662b898
Source dataset
uspto-grants-1997_04
Patent number
US05620999

Reaction notes

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