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Potassium Carbonate → 1-(1,4-Dimethyl-1H-indol-3-ylmethyl)-3-isopropenyl-5,6-dimethyl-1,3-dihydro-benzimidazol-2-one

HRID 1747302
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인쇄 미리보기

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HRID 1747302 반응식
[C:1]([N:4]1[C:8]2[CH:9]=[C:10]([CH3:14])[C:11]([CH3:13])=[CH:12][C:7]=2[NH:6][C:5]1=[O:15])([CH3:3])=[CH2:2].C([O-])([O-])=O.[K+].[K+].[CH3:22][N:23]1[C:31]2[C:26](=[C:27]([CH3:32])[CH:28]=[CH:29][CH:30]=2)[C:25]([CH2:33][N+](C)(C)C)=[CH:24]1.[I-]>CN(C=O)C.C(OCC)(=O)C>[CH3:22][N:23]1[C:31]2[C:26](=[C:27]([CH3:32])[CH:28]=[CH:29][CH:30]=2)[C:25]([CH2:33][N:6]2[C:7]3[CH:12]=[C:11]([CH3:13])[C:10]([CH3:14])=[CH:9][C:8]=3[N:4]([C:1]([CH3:3])=[CH2:2])[C:5]2=[O:15])=[CH:24]1
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참가 물질

7

반응물 4

HCID 11430Potassium CarbonateHCID 30165Iodide IonHCID 130168351-Isopropenyl-5,6-dimethyl-1,3-dihydro-benzimidazol-2-oneHCID 17836487(1,4-Dimethyl-1H-indol-3-ylmethyl)-trimethyl-ammonium

생성물 1

HCID 594974911-(1,4-Dimethyl-1H-indol-3-ylmethyl)-3-isopropenyl-5,6-dimethyl-1,3-dihydro-benzimidazol-2-one

시약·촉매·용매 2

HCID 6228
Dimethylformamide
용매
HCID 8857Ethyl Acetate용매

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온도
90 °C

실험 절차

To a solution of 1-Isopropenyl-5,6-dimethyl-1,3-dihydro-benzimidazol-2-one (0.25 g, 1.2 mmol) in DMF (10 mL) was added K2CO3 (0.51 g, 3.7 mmol). The reaction mixture was heated to 90° C. and stirred for 20 min. (1,4-Dimethyl-1H-indol-3-ylmethyl)-trimethyl-ammonium; iodide (0.64 g, 1.8 mmol) was then added to the reaction mixture and stirred for another 3 h. The reaction mixture was treated with ethyl acetate and washed with water. The resulting residue was purified by silica gel prep TLC using 4:1 Hexane:ethyl acetate as an eluent to afford 0.35 g the desired product as an off-white solid. LCMS (ESMS): m/z 360.33 (M+H+).

후처리

  1. washwashed with water
  2. customThe resulting residue was purified by silica gel prep TLC

출처 및 근거

ORD 기록
ord-100010ce3c6e4c25a4103e48875d3d77
출처 데이터셋
uspto-grants-2015_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09150556B2

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