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Sodium hydride → Tert-butyl ethyl 3-fluoro-4-(hexadecylamino)benzoylmalonate

HRID 1389104
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HRID 1389104 반응식
[C:1]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])(=[O:8])[CH2:2][C:3]([O:5][CH2:6][CH3:7])=[O:4].[H-].[Na+].Cl.[F:17][C:18]1[CH:19]=[C:20]([CH:24]=[CH:25][C:26]=1[NH:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH3:43])[C:21](Cl)=[O:22]>COCCOC>[F:17][C:18]1[CH:19]=[C:20]([CH:24]=[CH:25][C:26]=1[NH:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH3:43])[C:21]([CH:2]([C:3]([O:5][CH2:6][CH3:7])=[O:4])[C:1]([O:9][C:10]([CH3:12])([CH3:11])[CH3:13])=[O:8])=[O:22]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 3

HCID 24758Sodium hydrideHCID 96345tert-Butyl ethyl malonateHCID 205364403-Fluoro-4-hexadecylaminobenzoyl chloride hydrochloride

생성물 1

HCID 53991576Tert-butyl ethyl 3-fluoro-4-(hexadecylamino)benzoylmalonate

시약·촉매·용매 1

HCID 80711,2-Dimethoxyethane용매3회

실험 절차

A solution of 28.0 g. of tert-butyl ethyl malonate in 10 ml. of 1,2-dimethoxyethane is added to a suspension of 4.0 g. of sodium hydride in 1,2-dimethoxyethane under argon. A solution of 17.3 g of 3-fluoro-4-(hexadecylamino)benzoyl chloride hydrochloride in 1,2-dimethoxyethane is then added. The reaction mixture is refluxed for 5 hours, cooled, poured on ice and extracted with ether. The ether solution is washed with water and saturated sodium chloride solution, dried over anhydrous sodium sulfate and concentrated to dryness. The residue is then recrystallized from ether to yield tert-butyl ethyl 3-fluoro-4-(hexadecylamino)benzoylmalonate.

후처리

  1. temperatureThe reaction mixture is refluxed for 5 hours
  2. temperaturecooled
  3. additionpoured on ice
  4. extractionextracted with ether
  5. washThe ether solution is washed with water and saturated sodium chloride solution
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated to dryness
  8. customThe residue is then recrystallized from ether

출처 및 근거

ORD 기록
ord-99484fd4cd644b5781da0e91dd8bf5c5
출처 데이터셋
uspto-grants-1981_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US04243609

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