Ethyl bromoacetate → ethyl 2-(1H-1,3-benzodiazol-2-ylsulfanyl)acetate

HRID 507261

Reaction equation

HRID 507261 reaction equation
[NH:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[NH:3][C:2]1=[S:10].C(=O)([O-])[O-].[K+].[K+].Br[CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20]>C(O)C>[NH:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[S:10][CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20]

Participants

5

Reactant 3

HCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 7070352-Mercaptobenzimidazole

Product 1

HCID 21564ethyl 2-(1H-1,3-benzodiazol-2-ylsulfanyl)acetateYield 30,947.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a stirred solution of 1H-benzo[d]imidazole-2(3H)-thione (20.0 g, 0.13 mol, 1.0 eq.) in anhydrous ethanol (500 mL) at room temperature, was added potassium carbonate (9.25 g, 0.07 mol, 0.5 eq.) and ethyl bromoacetate (26.7 g, 0.16 mmol, 1.2 eq.). The reaction was heated to reflux and stirred at that temperature for 6 hours. The solvent was removed in vacuo and water (200 mL) was added. The aqueous phase was extracted with dichloromethane (3×100 mL), and the combined organic extracts were washed with water (200 mL) and brine (200 mL). The organic phase was dried over magnesium sulfate and concentrated in vacuo to give a colorless oil which solidified on standing. Purification by flash chromatography (CHCl3→10% MeOH:90% CHCl3) gave 4a as a white solid (11.7 g, 37%).

Workup

  1. temperatureThe reaction was heated
  2. temperatureto reflux
  3. customThe solvent was removed in vacuo and water (200 mL)
  4. additionwas added
  5. extractionThe aqueous phase was extracted with dichloromethane (3×100 mL)
  6. washthe combined organic extracts were washed with water (200 mL) and brine (200 mL)
  7. dry with materialThe organic phase was dried over magnesium sulfate
  8. concentrationconcentrated in vacuo
  9. customto give a colorless oil which
  10. customPurification by flash chromatography (CHCl3→10% MeOH:90% CHCl3)

Sources & evidence

ORD record
ord-5334d5798f48437cbdff6f8e3432540f
Source dataset
uspto-grants-2010_08
Patent number
US07786139B2

Linked notes

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