2-Aminophenol → 4-fluoro-N-(2-hydroxyphenyl)-3-nitrobenzanilide

HRID 74173

반응식

HRID 74173 반응식
[F:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=O)=[CH:4][C:3]=1[N+:11]([O-:13])=[O:12].[NH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[OH:21].Cl.C(N=C=N[CH2:28][CH2:29][CH2:30]N(C)C)C.C(N([CH2:39][CH3:40])CC)C.[CH:41](Cl)(Cl)Cl>C(OCC)(=O)C>[F:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([N:14]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[OH:21])[C:28]2[CH:29]=[CH:30][CH:40]=[CH:39][CH:41]=2)=[O:8])=[CH:4][C:3]=1[N+:11]([O-:13])=[O:12]

참가 물질

7

반응물 5

HCID 58012-AminophenolHCID 6212ChloroformHCID 8471TriethylamineHCID 679874-Fluoro-3-nitrobenzoic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

생성물 1

HCID 674979344-fluoro-N-(2-hydroxyphenyl)-3-nitrobenzanilide수율 68%

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매

실험 절차

To a solution of 4-fluoro-3-nitrobenzoic acid (2.00 g, 10.8 mmol) in chloroform (40 mL) was added 2-aminophenol (1.18 g, 10.8 mmol), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (2.17 g, 11.3 mmol), and triethylamine (1.15 g, 11.3 mmol), and this was stirred at room temperature for 2.5 hours. After the reaction was complete, this was diluted by adding ethyl acetate, and this was washed with water, 1N hydrochloric acid, and saturated aqueous sodium hydrogen carbonate. The organic layer obtained was dried over anhydrous sodium sulfate, after which it was filtered and concentrated to yield the title compound (2.02 g, 68% yield) as orange crystals.

후처리

  1. additionthis was diluted
  2. washthis was washed with water, 1N hydrochloric acid, and saturated aqueous sodium hydrogen carbonate
  3. customThe organic layer obtained
  4. dry with materialwas dried over anhydrous sodium sulfate
  5. filtrationafter which it was filtered
  6. concentrationconcentrated

출처 및 근거

ORD 기록
ord-e51a015c6d30428c8a4b915518a238cb
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08829035B2

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