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

HRID 1256595ノート

反応式

HRID 1256595 の反応式
[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

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
80 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-1515521152354cd49d7dd40bbfb5e865
出典データセット
uspto-grants-2013_06
特許番号
US08461181B2

反応ノート

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