Dimethylformamide → 6-Chloro-4-(1-chloroethyl)-3-ethoxy-2-(2-oxo-1,3-oxazolidin-5-yl)benzonitrile

HRID 1499939ノート

反応式

HRID 1499939 の反応式
[Cl:1][C:2]1[C:7]([C:8]#[N:9])=[C:6]([CH:10]2[O:14][C:13](=[O:15])[NH:12][CH2:11]2)[C:5]([O:16][CH2:17][CH3:18])=[C:4]([CH:19](O)[CH3:20])[CH:3]=1.CN(C)C=O.S(Cl)([Cl:29])=O>C(Cl)Cl>[Cl:1][C:2]1[C:7]([C:8]#[N:9])=[C:6]([CH:10]2[O:14][C:13](=[O:15])[NH:12][CH2:11]2)[C:5]([O:16][CH2:17][CH3:18])=[C:4]([CH:19]([Cl:29])[CH3:20])[CH:3]=1

参加物

5

反応物 3

HCID 6228DimethylformamideHCID 24386Thionyl ChlorideHCID 866778556-Chloro-3-ethoxy-4-(1-hydroxyethyl)-2-(2-oxo-1,3-oxazolidin-5-yl)benzonitrile

生成物 1

HCID 866778566-Chloro-4-(1-chloroethyl)-3-ethoxy-2-(2-oxo-1,3-oxazolidin-5-yl)benzonitrile

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

To a mixture of 6-chloro-3-ethoxy-4-(1-hydroxyethyl)-2-(2-oxo-1,3-oxazolidin-5-yl)benzonitrile (58 mg, 0.19 mmol) (mixture of four diastereomers from step 4), N,N-dimethylformamide (36 μL) in methylene chloride (1 mL), thionyl chloride (40.0 μL, 0.56 mmol) was added and the mixture was stirred at room temperature for 20 minutes The mixture was diluted with methylene chloride, washed with saturated sodium bicarbonate, water, brine, dried over sodium sulfate, filtered and concentrated to give the desired compound as a mixture of four diastereomers, 55 mg, 91%. LCMS calculated for C14H15Cl2N2O3 (M+H)+: m/z=329.0; found: 329.1.

後処理

  1. additionwas added
  2. washwashed with saturated sodium bicarbonate, water, brine
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated

出典と根拠

ORDレコード
ord-8aaa9ef4900b4dfb9e6f1b02a04672b1
出典データセット
uspto-grants-2015_12
特許番号
US09199982B2

反応ノート

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