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Cesium carbonate → methyl N-[[2-chloro-5-[2-(4-chlorophenyl)-2H-1,2,3-triazol-4-yl]phenyl]methyl]carbamate

HRID 70249
ノート
印刷プレビュー

反応式

HRID 70249 の反応式
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[NH:12][N:11]=[N:10][CH:9]=2)=[CH:4][C:3]=1[CH2:13][NH:14][C:15](=[O:18])[O:16][CH3:17].[Cl:19][C:20]1[CH:25]=[CH:24][C:23](I)=[CH:22][CH:21]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C)C=O.C/C(/[O-])=C/C(C)=O.C/C(/[O-])=C/C(C)=O.C/C(/[O-])=C/C(C)=O.[Fe+3].[Cu]=O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]=[N:10][N:11]([C:23]3[CH:24]=[CH:25][C:20]([Cl:19])=[CH:21][CH:22]=3)[N:12]=2)=[CH:4][C:3]=1[CH2:13][NH:14][C:15](=[O:18])[O:16][CH3:17]
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

7

反応物 3

HCID 10796Cesium carbonateHCID 125101-Chloro-4-iodobenzeneHCID 178502068HCID 178502068、化合物

生成物 1

HCID 66790465methyl N-[[2-chloro-5-[2-(4-chlorophenyl)-2H-1,2,3-triazol-4-yl]phenyl]methyl]carbamate

試薬・触媒・溶媒 3

HCID 14829Copper oxide触媒
HCID 5483663
Ferric acetylacetonate
触媒
HCID 6228Dimethylformamide溶媒

反応条件

温度
110 °C

実験手順

A mixture of methyl N-[[2-chloro-5-(1H-1,2,3-triazol-5-yl)phenyl]methyl]carbamate (i.e. the product of Step E, Example 9) (0.53 g, 2.0 mmol), 1-chloro-4-iodobenzene (0.57 g, 2.4 mmol), iron(III) acetylacetonate (0.21 g, 0.6 mmol), copper(II) oxide (0.016 g, 0.2 mmol) and cesium carbonate (1.29 g, 4.0 mmol) in N,N-dimethylformamide (4 mL) was heated at 110° C. for 14 h and then concentrated under reduced pressure. The resulting residue was suspended in ethanol and then concentrated onto silica gel (2 g). The silica gel mixture was purified by flash column chromatography using a Supelco (division of Sigma-Aldrich Co., 595 North Harrison Road, Bellefonte, Pa. 16823, U.S.A.) tube prepacked with 10 g of silica gel (50 μm particle diameter, 70 Å pore size) and 3:1 hexanes-ethyl acetate as eluant to provide methyl N-[[2-chloro-5-[2-(4-chlorophenyl)-2H-1,2,3-triazol-4-yl]phenyl]methyl]carbamate, a compound of the present invention, as a beige solid (0.105 g)

後処理

  1. concentrationconcentrated under reduced pressure
  2. concentrationconcentrated onto silica gel (2 g)
  3. customThe silica gel mixture was purified by flash column chromatography

出典と根拠

ORDレコード
ord-0ff2427f72cc46ffbf9d3971494da081
出典データセット
uspto-grants-2014_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08822521B2

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