Oxalyl chloride → 4-Chloro-3-(3,5-dichloro-pyridin-2-yl)benzoyl chloride

HRID 448894ノート

反応式

HRID 448894 の反応式
[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](O)=[O:7])=[CH:4][C:3]=1[C:11]1[C:16]([Cl:17])=[CH:15][C:14]([Cl:18])=[CH:13][N:12]=1.C(Cl)(=O)C([Cl:22])=O>C(Cl)Cl.CN(C=O)C>[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([Cl:22])=[O:7])=[CH:4][C:3]=1[C:11]1[C:16]([Cl:17])=[CH:15][C:14]([Cl:18])=[CH:13][N:12]=1

参加物

5

反応物 2

HCID 65578Oxalyl chlorideHCID 686040024-Chloro-3-(3,5-dichloro-pyridin-2-yl)-benzoic acid

生成物 1

HCID 866425734-Chloro-3-(3,5-dichloro-pyridin-2-yl)benzoyl chloride

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide触媒HCID 6344Dichloromethane溶媒

実験手順

To 4-chloro-3-(3,5-dichloro-pyridin-2-yl)-benzoic acid (100 mg, 0.33 mmol) in dry DCM (1 mL), was added DMF (1 drop) followed by addition of oxalyl chloride (35 μL, 0.40 mmol) slowly. The mixture was stirred for 2.5 hrs, then concentrated to yield 4-chloro-3-(3,5-dichloro-pyridin-2-yl)-benzoyl chloride, which was dissolved in DCM (1 mL). 2-Methylamino-phenol (45 mg, 0.36 mmol) was added followed by the slow addition of diisopropylethylamine (88 μL, 0.5 mmol). The mixture was stirred at room temperature for 12 hrs, concentrated and purified by preparative TLC (DCM/MeOH=9/1) followed by preparative LCMS to yield 4-chloro-3-(3,5-dichloro-pyridin-2-yl)-N-(2-hydroxy-phenyl)-N-methyl-benzamide 19-1. MS (M+H)+: 409.0, tR=7.55 min (method 2)

後処理

  1. concentrationconcentrated

出典と根拠

ORDレコード
ord-2c67edc14a234f59b9427747549f2f70
出典データセット
uspto-grants-2013_07
特許番号
US08481738B2

反応ノート

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