1-Bromooctane → 1H-Benzimidazole, 2-(octylthio)-

HRID 1030577Notes

Reaction equation

HRID 1030577 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+].O.[CH2:14](Br)[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21]>CO>[CH2:14]([S:1][C:2]1[NH:6][C:5]2[CH:7]=[CH:8][CH:9]=[CH:10][C:4]=2[N:3]=1)[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21]

Participants

5

Reactant 3

HCID 81401-BromooctaneHCID 23719242Sodium hydroxide--water (1/1/1)HCID 178527775HCID 178527775, compound

Product 1

HCID 31159711H-Benzimidazole, 2-(octylthio)-Yield 72%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 2-mercaptobenzimidazole (4.95 g, 33 mmol) in methanol (150 mL) and 2N NaOH/H2O (50 mmol) was added octyl bromide (7.16 g, 33 mmol). The solution was stirred at ambient temperature for 72 hours, during which a suspension formed which was filtered and the solid residue dissolved in CH2Cl2, washed with saturated NaHCO3, and dried over Na2SO4. Evaporation of the solvent gave the title compound as a white solid (6.2 g, 72%). m.p. 110°-113° C. NMR CDCl3)δ7.4(m, 4H), 3.22(t, J=8 Hz, 2H), 1.20(br, 15H).

Workup

  1. customformed which
  2. filtrationwas filtered
  3. dissolutionthe solid residue dissolved in CH2Cl2
  4. washwashed with saturated NaHCO3
  5. dry with materialdried over Na2SO4
  6. customEvaporation of the solvent

Sources & evidence

ORD record
ord-a2a9cb0dc00e46f2bc7952b6c747d5c4
Source dataset
uspto-grants-1992_04
Patent number
US05106863

Reaction notes

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