Water → HCID 22643424, compound

HRID 2414786Notes

Reaction equation

HRID 2414786 reaction equation
[CH3:1][C:2]1[CH:11]=[CH:10][C:5]2[N:6]=[C:7]([SH:9])[NH:8][C:4]=2[CH:3]=1.C([O:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20]Br)(=O)C.[OH-].[Na+].O>C(O)C>[OH:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][S:9][C:7]1[NH:8][C:4]2[CH:3]=[C:2]([CH3:1])[CH:11]=[CH:10][C:5]=2[N:6]=1

Participants

6

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 851405-Bromopentyl acetateHCID 178423448HCID 178423448, compound

Product 1

HCID 22643424HCID 22643424, compoundYield 81.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2.46 g of 5-methyl-2-mercaptobenzimidazole and 3.4 g of 5-bromopentyl acetate were dissolved in 30 ml of ethanol and the mixture was refluxed with stirring under heating for 7 hours. After cooling to room temperature, the reaction mixture was added with was 22.5 ml of 2 N sodium hydroxide solution and stirred at room temperature for 1 hour, and then poured into water and extracted with ethyl acetate. The ethyl acetate layer was washed with saturated brine and dried over sodium sulfate and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (methylene chloride:methanol=95:5) to obtain 3.04 g of the title compound as pale yellow oil (yield: 81%).

Workup

  1. temperaturethe mixture was refluxed
  2. temperatureunder heating for 7 hours
  3. additionthe reaction mixture was added
  4. stirringstirred at room temperature for 1 hour
  5. extractionextracted with ethyl acetate
  6. washThe ethyl acetate layer was washed with saturated brine
  7. dry with materialdried over sodium sulfate
  8. customthe solvent was evaporated under reduced pressure
  9. customThe residue was purified by silica gel column chromatography (methylene chloride:methanol=95:5)

Sources & evidence

ORD record
ord-b735b6d5093a470e828235d1720db278
Source dataset
uspto-grants-2004_11
Patent number
US06815455B1

Reaction notes

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