p-Toluenesulfonic acid → 4-(5,6-dimethyl-1H-benzo[d]imidazol-2-yl)-2-fluorobenzo-nitrile

HRID 75522

반응식

HRID 75522 반응식
[F:1][C:2]1[CH:9]=[C:8]([CH:10]=O)[CH:7]=[CH:6][C:3]=1[C:4]#[N:5].[CH3:12][C:13]1[CH:14]=[C:15]([NH2:21])[C:16]([NH2:20])=[CH:17][C:18]=1[CH3:19].C1(C)C=CC(S(O)(=O)=O)=CC=1>C(O)C>[CH3:12][C:13]1[C:18]([CH3:19])=[CH:17][C:16]2[NH:20][C:10]([C:8]3[CH:7]=[CH:6][C:3]([C:4]#[N:5])=[C:2]([F:1])[CH:9]=3)=[N:21][C:15]=2[CH:14]=1

참가 물질

5

반응물 3

HCID 6101p-Toluenesulfonic acidHCID 766354,5-Dimethyl-1,2-phenylenediamineHCID 112173392-Fluoro-4-formylbenzonitrile

생성물 1

HCID 676058844-(5,6-dimethyl-1H-benzo[d]imidazol-2-yl)-2-fluorobenzo-nitrile수율 68%

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

To a solution of 2-fluoro-4-formylbenzonitrile 1 (100 mg, 0.7 mmol) and 4,5-dimethyl benzene-1,2-diamine 2 (109 mg, 0.8 mmol) in ethanol (10 ml) was added a catalytic amount of p-toluenesulfonic acid (0.5 mg, 0.5 mmol). The mixture was stirred reflux for 2 hours and concentrated by rotor evaporation. The crude material was purified through column chromatography with 40% ethyl acetate in hexane to yield compound 3 as white solid (68% yield, 121 mg, confirmed by LCMS: 266.20).

후처리

  1. temperaturereflux for 2 hours
  2. concentrationconcentrated by rotor evaporation
  3. customThe crude material was purified through column chromatography with 40% ethyl acetate in hexane

출처 및 근거

ORD 기록
ord-bfcf62b3d635493ba4417b87b12b94db
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08835445B2

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