1-Bromooctane → HCID 178443879, compound

HRID 1030579Notes

Reaction equation

HRID 1030579 reaction equation
[Cl:1][C:2]1[CH:11]=[CH:10][C:5]2[N:6]=[C:7]([SH:9])[NH:8][C:4]=2[CH:3]=1.[OH-].[Na+].[CH2:14](Br)[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21]>CO>[Cl:1][C:2]1[CH:11]=[CH:10][C:5]2[NH:6][C:7]([S:9][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])=[N:8][C:4]=2[CH:3]=1

Participants

5

Reactant 3

HCID 81401-BromooctaneHCID 14798Sodium HydroxideHCID 178527787HCID 178527787, compound

Product 1

HCID 178443879HCID 178443879, compoundYield 75.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 5-chloro-2-mercaptobenzimidazole (1.84 c, 10 mmol) (Varima, R. S., J. Indian Chem. Soc. 62, 73 (1985)) in methanol (10 mL) and 2N sodium hydroxide (13 mmol) was added octyl bromide (2.17 g, 10 mmol). The solution was stirred at ambient temperature for 72 hours, evaporated, dissolved in CH2Cl2, washed with brine and dried over Na2SO4. Evaporation of the solvent and flash chromatography (Merck Kieselgel, 5% Et2O/CH2Cl2) gave a residue which solidified on standing. A pentane wash gave the title compound as a beige solid (2.23 g), m.p. 66°-67° C. NMR (CDCl3)δ7.3(m, 3H), 5.33(t, J=6 Hz, 2H), 1.20(br, 15H).

Workup

  1. customevaporated
  2. dissolutiondissolved in CH2Cl2
  3. washwashed with brine
  4. dry with materialdried over Na2SO4
  5. customEvaporation of the solvent and flash chromatography (Merck Kieselgel, 5% Et2O/CH2Cl2)
  6. customgave a residue which
  7. washA pentane wash

Sources & evidence

ORD record
ord-e9d6bf8e10f34d2496191bbd7b15463c
Source dataset
uspto-grants-1992_04
Patent number
US05106863

Reaction notes

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