Sodium Hydroxide → HCID 178488136, compound

HRID 1030573Notes

Reaction equation

HRID 1030573 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[CH:11][C:6]2[N:7]=[C:8]([SH:10])[NH:9][C:5]=2[CH:4]=1.[CH2:13](Cl)/[CH:14]=[C:15](/[CH2:17][CH2:18][CH:19]=[C:20]([CH3:22])[CH3:21])\[CH3:16].[OH-].[Na+]>CO>[CH3:16]/[C:15](/[CH2:17][CH2:18][CH:19]=[C:20]([CH3:22])[CH3:21])=[CH:14]\[CH2:13][S:10][C:8]1[NH:7][C:6]2[CH:11]=[CH:12][C:3]([O:2][CH3:1])=[CH:4][C:5]=2[N:9]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 6372219Geranyl chlorideHCID 178488032HCID 178488032, compound

Product 1

HCID 178488136HCID 178488136, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To the 5-methoxy-2-mercaptobenzimidazole (2.5 g, 0.014M) in methanol (100 mL) was added geranyl chloride (2.4 g, 0.014M). The solution was taken to pH 11 (2N NaOH), stirred overnight at ambient temperature, evaporated, dissolved in CH2Cl2, washed with saturated NaHCO3 +brine, and dried over Na2SO4. The solvent was evaporated to oil which was flash chromatographed (Rf=0.76) (5% MeOH (CH2Cl2)) to give 2-[(3,7-dimethyl-2,6-(E)-octadienyl)thio]-5-methoxy-1H-1,3-benzimidazole (free base) which was converted to its oxalate salt (0.74 g). m.p. 113°-116° C. NMR (DMSO-d6)δ7.8(m,3H), 5.2 (m, 2H), 3.9(d, J=7 Hz, 2H), 3.8(s, 3H), 2.02(m, 4H),1.7(s,3H), 1.6(s, 6H).

Workup

  1. customevaporated
  2. dissolutiondissolved in CH2Cl2
  3. washwashed with saturated NaHCO3 +brine
  4. dry with materialdried over Na2SO4
  5. customThe solvent was evaporated to oil which
  6. customchromatographed (Rf=0.76) (5% MeOH (CH2Cl2))

Sources & evidence

ORD record
ord-f1d6be6a8fb64b9c8bbdf204d42ff2d8
Source dataset
uspto-grants-1992_04
Patent number
US05106863

Reaction notes

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