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

HRID 507261

반응식

HRID 507261 반응식
[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]

참가 물질

5

반응물 3

HCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 7070352-Mercaptobenzimidazole

생성물 1

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

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

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%).

후처리

  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)

출처 및 근거

ORD 기록
ord-5334d5798f48437cbdff6f8e3432540f
출처 데이터셋
uspto-grants-2010_08
특허 번호
US07786139B2

연결된 노트

불러오는 중…