Pyridine → 7-bromo-2-(2-ethylsulfanylphenyl)-1-methyl-5-trifluoromethyl-1H-benzimidazole

HRID 533620노트

반응식

HRID 533620 반응식
[Br:1][C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:5]=[C:4]([NH2:12])[C:3]=1[NH:13][CH3:14].[CH2:15]([S:17][C:18]1[CH:26]=[CH:25][CH:24]=[CH:23][C:19]=1[C:20](O)=O)[CH3:16].CCN=C=NCCCN(C)C.N1C=CC=CC=1>O>[Br:1][C:2]1[C:3]2[N:13]([CH3:14])[C:20]([C:19]3[CH:23]=[CH:24][CH:25]=[CH:26][C:18]=3[S:17][CH2:15][CH3:16])=[N:12][C:4]=2[CH:5]=[C:6]([C:8]([F:9])([F:10])[F:11])[CH:7]=1

참가 물질

6

반응물 4

HCID 1049PyridineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 4257582-(Ethylsulfanyl)benzoic acidHCID 860613183-bromo-N2-methyl-5-trifluoromethylbenzene-1,2-diamine

생성물 1

HCID 679843387-bromo-2-(2-ethylsulfanylphenyl)-1-methyl-5-trifluoromethyl-1H-benzimidazole수율 43.2%

시약·촉매·용매 1

HCID 962Water용매

반응 조건

온도
115 °C

실험 절차

A mixture of 3-bromo-N2-methyl-5-trifluoromethylbenzene-1,2-diamine (2.22 g), 2-ethylsulfanylbenzoic acid (1.80 g), WSC (1.40 g), and pyridine (10 ml) was stirred under reflux at 115° C. for 6 hours. Into the reaction mixture cooled to room temperature, water was poured, and extracted with ethyl acetate. The organic layer was dried over magnesium sulfate, and concentrated under reduced pressure. The resulting residue was subjected to silica gel column chromatography to give 1.48 g of 7-bromo-2-(2-ethylsulfanylphenyl)-1-methyl-5-trifluoromethyl-1H-benzimidazole (hereinafter referred to as Present Compound 74).

후처리

  1. temperatureInto the reaction mixture cooled to room temperature
  2. extractionextracted with ethyl acetate
  3. dry with materialThe organic layer was dried over magnesium sulfate
  4. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-e941f0879f0546ac9e7860b8073f78cb
출처 데이터셋
uspto-grants-2014_10
특허 번호
US08853238B2

반응 노트

불러오는 중…