Dimethyl Sulfoxide → N-(3-formylphenyl)-2-methoxyacetamide

HRID 1669343

反応式

HRID 1669343 の反応式
C(Cl)(=O)C(Cl)=O.CS(C)=O.[CH3:11][O:12][CH2:13][C:14]([NH:16][C:17]1[CH:18]=[C:19]([CH:22]=[CH:23][CH:24]=1)[CH2:20][OH:21])=[O:15].C(N(CC)CC)C>ClCCl.O>[CH3:11][O:12][CH2:13][C:14]([NH:16][C:17]1[CH:18]=[C:19]([CH:22]=[CH:23][CH:24]=1)[CH:20]=[O:21])=[O:15]

参加物

7

反応物 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 606384223-(Methoxyacetylamino)benzyl alcohol

生成物 1

HCID 11615331N-(3-formylphenyl)-2-methoxyacetamide収率 95%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6344Dichloromethane溶媒3 回

反応条件

温度
-60 °C

実験手順

To a mixture of 11.40 g of oxalyl chloride and 200 ml of dichloromethane was added dropwise a solution of 14 ml of dimethyl sulfoxide in 30 ml of dichloromethane at −60° C. for 15 minutes. After stirred at −60° C. for 10 minutes, a solution of 15.88 g of 3-(methoxyacetylamino)benzyl alcohol in 70 ml of dichloromethane was added dropwise at −60° C. for 20 minutes. After stirred at −60° C. for 10 minutes, 24.82 g of triethylamine was added dropwise at −60° C. for 20 minutes. After stirred at room temperature for 45 minutes, 500 ml of water was added to the reaction solution, followed by extraction with 300 ml of ethyl acetate. The organic layer was washed with an aqueous saturated sodium chloride solution, dried over anhydrous magnesium sulfate, and then concentrated to obtain 14.93 g of 3-(methoxyacetylamino)benzaldehyde [Compound No. (a)] as a white crystal.

後処理

  1. stirringAfter stirred at −60° C. for 10 minutes
  2. stirringAfter stirred at room temperature for 45 minutes
  3. extractionfollowed by extraction with 300 ml of ethyl acetate
  4. washThe organic layer was washed with an aqueous saturated sodium chloride solution
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated

出典と根拠

ORDレコード
ord-92846a3c38834b568cc490936569ca80
出典データセット
uspto-grants-2011_08
特許番号
US07989478B2

関連ノート

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