Ammonium Chloride → 2-(3-fluoropyridin-4-yl)-1-methyl-5-trifluoromethyl-1H-benzimidazole

HRID 1256595

반응식

HRID 1256595 반응식
[CH3:1][NH:2][C:3]1[C:4]([NH2:13])=[CH:5][C:6]([C:9]([F:12])([F:11])[F:10])=[CH:7][CH:8]=1.[F:14][C:15]1[CH:16]=[N:17][CH:18]=[CH:19][C:20]=1[CH:21]=O.S(=O)(O)[O-].[Na+].[Cl-].[NH4+]>CN(C=O)C>[F:14][C:15]1[CH:16]=[N:17][CH:18]=[CH:19][C:20]=1[C:21]1[N:2]([CH3:1])[C:3]2[CH:8]=[CH:7][C:6]([C:9]([F:10])([F:11])[F:12])=[CH:5][C:4]=2[N:13]=1

참가 물질

6

반응물 4

HCID 25517Ammonium ChlorideHCID 715666N1-Methyl-4-(trifluoromethyl)benzene-1,2-diamineHCID 27630033-FluoroisonicotinaldehydeHCID 23665763Sodium Bisulfite

생성물 1

HCID 666115222-(3-fluoropyridin-4-yl)-1-methyl-5-trifluoromethyl-1H-benzimidazole수율 62%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

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온도
80 °C

실험 절차

A mixture of 1.90 g of N1-methyl-4-trifluoromethylbenzene-1,2-diamine, 1.49 g of 3-fluoropyridine-4-carbaldehyde, 3.12 g of sodium bisulfite and 20 ml of DMF was stirred for 1.5 hours while heating at 80° C., then, was stirred for 2 hours while heating at 120° C. After cooling down to room temperature, a saturated ammonium chloride aqueous solution was poured, and the mixture was extracted three times with ethyl acetate. The combined organic layers were dried over magnesium sulfate, then, concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to obtain 1.83 g of 2-(3-fluoropyridin-4-yl)-1-methyl-5-trifluoromethyl-1H-benzimidazole (hereinafter, referred to as present active compound 4).

후처리

  1. stirringwas stirred for 2 hours
  2. temperaturewhile heating at 120° C
  3. temperatureAfter cooling down to room temperature
  4. extractionthe mixture was extracted three times with ethyl acetate
  5. dry with materialThe combined organic layers were dried over magnesium sulfate
  6. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-1515521152354cd49d7dd40bbfb5e865
출처 데이터셋
uspto-grants-2013_06
특허 번호
US08461181B2

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