Sodium Hydroxide → HCID 178443465, compound

HRID 1030575Notes

Reaction equation

HRID 1030575 reaction equation
[F:1][C:2]([F:14])([F:13])[C:3]1[CH:12]=[CH:11][C:6]2[N:7]=[C:8]([SH:10])[NH:9][C:5]=2[CH:4]=1.[OH-].[Na+].[CH2:17](Cl)/[CH:18]=[C:19](/[CH2:21][CH2:22][CH:23]=[C:24]([CH3:26])[CH3:25])\[CH3:20]>CO>[F:14][C:2]([F:13])([F:1])[C:3]1[CH:12]=[CH:11][C:6]2[NH:7][C:8]([S:10][CH2:17]/[CH:18]=[C:19](\[CH3:20])/[CH2:21][CH2:22][CH:23]=[C:24]([CH3:26])[CH3:25])=[N:9][C:5]=2[CH:4]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 6372219Geranyl chlorideHCID 178506086HCID 178506086, compound

Product 1

HCID 178443465HCID 178443465, compoundYield 31%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 5-trifluoromethyl-2-mercaptobenzimidazole (1.09 g, 5 mmol) (Senn-Bilfingen, J., DE 3240298(1983)) in methanol (10 mL) was added 2N aqueous sodium hydroxide (6 mmol) and geranyl chloride (0.86 g, 5 mmol). The resultant solution was stirred for 48 hours at ambient temperature, evaporated in vacuo, dissolved in methylene chloride, washed with saturated sodium chloride, and dried over sodium sulfate. Evaporation of the solvent gave an oil which was flash chromatographed (5% MeOH (CH2Cl2) in Merck Kieselgel) and treated with charcoal. Evaporation of the solvent gave an off-white solid of the title compound (550 mg). m.p. 106°-108° C. NMR (CDCl3)δ7.83(m,1H), 7.57(m,2H), 5.43(d, J=7 Hz,1H), 5.2(m,1H), 4.03(d,J=7Hz,2H), 2.0(m,4H), 1.70(s,3H), 1.67(s,3H), 1.65(s,3H).

Workup

  1. customevaporated in vacuo
  2. dissolutiondissolved in methylene chloride
  3. washwashed with saturated sodium chloride
  4. dry with materialdried over sodium sulfate
  5. customEvaporation of the solvent
  6. customgave an oil which
  7. customchromatographed (5% MeOH (CH2Cl2) in Merck Kieselgel)
  8. additiontreated with charcoal
  9. customEvaporation of the solvent

Sources & evidence

ORD record
ord-c1fcea314f8244f1a7dfeaef82e258fd
Source dataset
uspto-grants-1992_04
Patent number
US05106863

Reaction notes

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