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Catechol → N-[2-fluoro-5-(2-hydroxyphenoxy)-4-nitrophenyl]acetamide

HRID 433724
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HRID 433724 반응식
[C:1]1([C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[OH:4])[OH:2].C(=O)([O-])[O-].[K+].[K+].CN(C)C=O.[F:20][C:21]1[CH:26]=[C:25]([N+:27]([O-:29])=[O:28])[C:24](F)=[CH:23][C:22]=1[NH:31][C:32](=[O:34])[CH3:33]>O>[F:20][C:21]1[CH:26]=[C:25]([N+:27]([O-:29])=[O:28])[C:24]([O:2][C:1]2[CH:8]=[CH:7][CH:6]=[CH:5][C:3]=2[OH:4])=[CH:23][C:22]=1[NH:31][C:32](=[O:34])[CH3:33]
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참가 물질

6

반응물 4

HCID 289CatecholHCID 6228Dimethylformamide2회HCID 11430Potassium CarbonateHCID 14624893N-(2,5-Difluoro-4-nitrophenyl)acetamide

생성물 1

HCID 21933568N-[2-fluoro-5-(2-hydroxyphenoxy)-4-nitrophenyl]acetamide수율 83.7%

시약·촉매·용매 1

HCID 962
Water
용매

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온도
60 °C

실험 절차

1.1 g of catechol and 2.76 g of potassium carbonate were added to 20 ml of N,N-dimethylformamide, and the mixture was heated to 60° C. Into this mixture was added dropwise a solution comprising 2.16 g of N-(2,5-difluoro-4-nitrophenyl)acetamide and 10 ml of N,N-dimethylformamide at temperatures from 65 to 70° C. The temperature of the mixture was kept for 1 hour, then, the mixture was cooled to room temperature, poured into water, extracted with ethyl acetate, and the organic layer was washed with dilute hydrochloric acid, washed with water, dried over magnesium sulfate, concentrated, and the resulted crystal was washed with t-butyl methyl ether to obtain 2.56 g of N-[2-fluoro-5-(2-hydroxyphenoxy)-4-nitrophenyl]acetamide.

후처리

  1. additionInto this mixture was added dropwise a solution
  2. customfrom 65 to 70° C
  3. temperaturethe mixture was cooled to room temperature
  4. extractionextracted with ethyl acetate
  5. washthe organic layer was washed with dilute hydrochloric acid
  6. washwashed with water
  7. dry with materialdried over magnesium sulfate
  8. concentrationconcentrated
  9. washthe resulted crystal was washed with t-butyl methyl ether

출처 및 근거

ORD 기록
ord-cf223cd60e114f12ba91a5fa83033a92
출처 데이터셋
uspto-grants-2003_12
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06667413B2

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