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Hydrochloric Acid → N-[2-(Methylsulfanyl)ethyl]-4-nitroaniline

HRID 1393835
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HRID 1393835 반응식
Cl.Cl.[NH2:3][CH2:4][CH2:5][SH:6].[CH3:7]I.[OH-].[Na+].F[C:12]1[CH:17]=[CH:16][C:15]([N+:18]([O-:20])=[O:19])=[CH:14][CH:13]=1.Cl>O.C(N(CC)CC)C>[CH3:7][S:6][CH2:5][CH2:4][NH:3][C:12]1[CH:17]=[CH:16][C:15]([N+:18]([O-:20])=[O:19])=[CH:14][CH:13]=1
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참가 물질

8

반응물 5

HCID 313Hydrochloric AcidHCID 6328Methyl iodideHCID 9590p-FluoronitrobenzeneHCID 14798Sodium HydroxideHCID 101541332-aminoethanethiol Dihydrochloride

생성물 1

HCID 14646022N-[2-(Methylsulfanyl)ethyl]-4-nitroaniline수율 35.3%

시약·촉매·용매 2

HCID 962Water용매2회
HCID 8471Triethylamine용매

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온도
28.5 °C

실험 절차

2-aminoethanethiol dihydrochloride (45.4 g, 0.4 mol), water (100 mL), and 56.8 g (0.4 mol) of methyl iodide were mixed together. 16.5 g of sodium hydroxide pellets (0.4 mol) were dissolved in 100 mL of water and this solution was poured dropwise into the reaction mixture, while maintaining the temperature between 27-30° C. The resulting mixture was then stirred for 1 hour at 40° C. 21.2 g (10.2 mol) of para-fluoronitrobenzene and then 42 mL of triethylamine were added and the mixture was maintained in a boiling water bath for 3 hours. The resulting mixture was left overnight at room temperature and then acidified with hydrochloric acid and extracted with ethyl acetate. After evaporation to dryness, the 30 g of oil obtained were dissolved in 100 mL of 36% HCl. The resulting solution was extracted with ethyl ether to remove the starting material and, when cold, the aqueous phase was neutralized with aqueous ammonia. The resulting aqueous phase was extracted again with ethyl ether, dried, and evaporated to dryness to give 11 g of oil.

후처리

  1. additionthis solution was poured dropwise into the reaction mixture
  2. temperaturethe mixture was maintained in a boiling water bath for 3 hours
  3. waitThe resulting mixture was left overnight at room temperature
  4. extractionextracted with ethyl acetate
  5. customAfter evaporation to dryness

출처 및 근거

ORD 기록
ord-c02fcda532a04d059adeaac026f0bf8a
출처 데이터셋
uspto-grants-2008_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07347879B2

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