Sodium Bicarbonate → HCID 86745705, compound

HRID 1030582Notes

Reaction equation

HRID 1030582 reaction equation
[OH:1][CH2:2][C:3]1(S)[N:7]=[C:6]2[CH:8]=[CH:9][CH:10]=[CH:11][C:5]2=[N:4]1.[CH2:13](Cl)/[CH:14]=[C:15](/[CH2:17][CH2:18][CH:19]=[C:20]([CH3:22])[CH3:21])\[CH3:16].C([O-])(O)=O.[Na+]>[I-].C([N+](CCCC)(CCCC)CCCC)CCC.C(Cl)Cl>[CH3:16]/[C:15](/[CH2:17][CH2:18][CH:19]=[C:20]([CH3:22])[CH3:21])=[CH:14]\[CH2:13][N:4]1[C:5]2[CH:11]=[CH:10][CH:9]=[CH:8][C:6]=2[N:7]=[C:3]1[CH2:2][OH:1]

Participants

6

Reactant 3

HCID 516892Sodium BicarbonateHCID 6372219Geranyl chlorideHCID 198207102-Mercapto-2H-benzimidazole-2-methanol

Product 1

HCID 86745705HCID 86745705, compound

Reagents, catalysts & solvents 2

HCID 67553Tetrabutylammonium IodideCatalystHCID 6344DichloromethaneSolvent

Procedure

A solution of 2-hydroxymethyl-2-mercaptobenzimidazole (2.68 g, 20 mmol), geranyl chloride (3.44 g, 20 mmol), tetrabutylammonium iodide (0.740 g, 2 mmol), saturated NaHCO3 (50 mL) and CH2Cl2 (40 mL) was stirred at ambient temperature for 72 hours. The methylene chloride layer was separated, washed with water and dried over Na2SO4. Evaporation and flash chromatography (Merck Kieselgel, 5% MeOH/CH2Cl2) gave 1-[3,7-dimethyl-2,6(E)-octadienyl]-2-hydroxymethyl-1H-1,3-benzimidazole free base) (1.45 g) which was converted to its hydrochloride salt, a gray solid. m.p. 120°-123° C. NMR (DMSO-d6)δ7.80(m,4H), 5.20(m,6H), 2.90(s,3H), 2.10(m,4H), 1.64(s,3H), 1.62(s,3H).

Workup

  1. customThe methylene chloride layer was separated
  2. washwashed with water
  3. dry with materialdried over Na2SO4
  4. customEvaporation and flash chromatography (Merck Kieselgel, 5% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-83f9c8f71d9542aba6b21477ef5426fc
Source dataset
uspto-grants-1992_04
Patent number
US05106863

Reaction notes

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