Sodium Hydroxide → HCID 19030808, compound

HRID 1005967Notes

Reaction equation

HRID 1005967 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.Br[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][OH:18].[OH-].[Na+]>C(O)(C)C>[OH:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][S:1][C:2]1[NH:3][C:4]2[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=2[N:6]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 779706-Bromo-1-hexanolHCID 178527775HCID 178527775, compound

Product 1

HCID 19030808HCID 19030808, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

3.0 g of 2-mercaptobenzimidazole and 3.8 g of 6-bromohexanol was added to 20 ml of isopropanol and refluxed with stirring for 5 hours. After cooling, the reaction mixture was neutralized with 2 N NaOH aqueous solution and extracted with ethyl acetate. The organic layer was washed with water and dried over sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel chromatography (20% ethyl acetate:methylene chloride) to obtain 5.0 g of the title compound (yield: 100%).

Workup

  1. temperaturerefluxed
  2. temperatureAfter cooling
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with water
  5. dry with materialdried over sodium sulfate
  6. customthe solvent was evaporated under reduced pressure
  7. customThe residue was purified by silica gel chromatography (20% ethyl acetate:methylene chloride)

Sources & evidence

ORD record
ord-3322307216c74d6391573310735770d2
Source dataset
uspto-grants-2004_09
Patent number
US06787561B1

Reaction notes

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