Dimethyl Sulfoxide → 5-Pentylbenzimidazol-2-one

HRID 2233544

반응식

HRID 2233544 반응식
[CH3:1][C:2]1[CH:11]=[CH:10][C:5]2=[N:6][C:7](=[O:9])[N:8]=[C:4]2[CH:3]=1.[O-]CC.[Na+].CS(C)=O.Br[CH2:21][CH2:22][CH2:23][CH3:24]>C(O)C>[CH2:1]([C:2]1[CH:11]=[CH:10][C:5]2=[N:6][C:7](=[O:9])[N:8]=[C:4]2[CH:3]=1)[CH2:21][CH2:22][CH2:23][CH3:24]

참가 물질

6

반응물 4

HCID 679Dimethyl SulfoxideHCID 8002Butyl bromideHCID 2723922Sodium ethoxideHCID 200643865-Methylbenzimidazol-2-one

생성물 1

HCID 671748435-Pentylbenzimidazol-2-one

시약·촉매·용매 1

HCID 702Ethanol용매2회

실험 절차

To a solution of 5-methylbenzimidazol-2-one (50 mg, 3.378×10−4 mol) in dry ethanol (5 ml), the freshly made sodium ethoxide in ethanol (1M, 1.01×10−3 mol equivalents) was added dropwise under a nitrogen atmosphere. At room temperature the mixture was stirred for 3 hrs under an atmosphere of nitrogen and the ethanol was then removed under reduced pressure. To this a solution of dry DMSO (3 ml) and 1-bromobutane (54 μl, 5.1×10−4 mol) was added and stirred at room temperature under an atmosphere of nitrogen overnight. The reaction mixture was then quenched with ice and neutralised using 1M hydrochloric acid solution, forming a white solid product. The solid was collected by filtration and purified using preparative thin liquid chromatography with 10% MeOH/CHCl3.

후처리

  1. customthe ethanol was then removed under reduced pressure
  2. stirringstirred at room temperature under an atmosphere of nitrogen overnight
  3. customThe reaction mixture was then quenched with ice
  4. customforming a white solid product
  5. filtrationThe solid was collected by filtration
  6. custompurified

출처 및 근거

ORD 기록
ord-54938d4a31ba44f994559747aa8c38a1
출처 데이터셋
uspto-grants-2010_05
특허 번호
US07709514B2

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