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Ammonia → 4-(benzyloxy)-1-(1,2-dimethyl-1H-benzimidazol-6-yl)pyridin-2(1H)-one

HRID 2203121
ノート
印刷プレビュー

反応式

HRID 2203121 の反応式
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][NH:12][C:11](=[O:15])[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Br[C:17]1[CH:18]=[CH:19][C:20]2[N:24]=[C:23]([CH3:25])[N:22]([CH3:26])[C:21]=2[CH:27]=1.CNCCNC.C(=O)([O-])[O-].[K+].[K+].N>CS(C)=O.[Cu]I.O>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][N:12]([C:17]2[CH:18]=[CH:19][C:20]3[N:24]=[C:23]([CH3:25])[N:22]([CH3:26])[C:21]=3[CH:27]=2)[C:11](=[O:15])[CH:10]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

9

反応物 5

HCID 222AmmoniaHCID 8070N,N'-DimethylethylenediamineHCID 11430Potassium CarbonateHCID 36077244-Benzyloxy-2(1H)-pyridoneHCID 581095096-bromo-1,2-dimethyl-1H-benzo[d]imidazole

生成物 1

HCID 896911954-(benzyloxy)-1-(1,2-dimethyl-1H-benzimidazol-6-yl)pyridin-2(1H)-one収率 59.1%

試薬・触媒・溶媒 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 679Dimethyl Sulfoxide溶媒HCID 962Water溶媒

反応条件

温度
90 °C

実験手順

To a suspension of 4-benzyloxy-2(1H)-pyridone (21.5 g), 6-bromo-1,2-dimethyl-1H-benzo[d]imidazole (16 g), N,N′-dimethylethylenediamine (7.57 ml) and potassium carbonate (29.5 g) in DMSO (160 ml) was added CuI (13.5 g), and the mixture was stirred at 90° C. for 5 h under Ar atmosphere. After the mixture was cooled, 28% NH3 solution (160 ml) and water (160 ml) were added. The precipitate was collected by filtration, washed with water and diisopropyl ether successively, and dried to give a solid. The residue was purified by silica gel column chromatography (hexane/EtOAc then EtOAc/MeOH) to give the title compound (14.5 g) as an off-white solid.

後処理

  1. temperatureAfter the mixture was cooled
  2. filtrationThe precipitate was collected by filtration
  3. washwashed with water and diisopropyl ether successively
  4. customdried
  5. customto give a solid
  6. customThe residue was purified by silica gel column chromatography (hexane/EtOAc

出典と根拠

ORDレコード
ord-8c688483617946759b2d70be31344717
出典データセット
uspto-grants-2016_06
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09365540B2

反応ノート

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このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート