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

HRID 639713

반응식

HRID 639713 반응식
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]

참가 물질

7

반응물 4

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

생성물 1

HCID 11615331N-(3-formylphenyl)-2-methoxyacetamide수율 95%

시약·촉매·용매 2

HCID 962Water용매HCID 6344Dichloromethane용매3회

반응 조건

온도
-60 °C

실험 절차

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 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.

후처리

  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 washed with an aqueous saturated sodium chloride solution
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated

출처 및 근거

ORD 기록
ord-7cbf437d179841f690e3d686017de98a
출처 데이터셋
uspto-grants-2010_04
특허 번호
US07691883B2

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