Triethylamine → N-(4-chloro-2-fluoro-5-nitrophenylaminothiocarbonyl)perhydropyridazine

HRID 1164709노트

반응식

HRID 1164709 반응식
I.[NH:2]1[CH2:7][CH2:6][CH2:5][CH2:4][NH:3]1.C(N(CC)CC)C.[Cl:15][C:16]1[C:21]([N+:22]([O-:24])=[O:23])=[CH:20][C:19]([N:25]=[C:26]=[S:27])=[C:18]([F:28])[CH:17]=1>C(Cl)Cl>[Cl:15][C:16]1[C:21]([N+:22]([O-:24])=[O:23])=[CH:20][C:19]([NH:25][C:26]([N:2]2[CH2:7][CH2:6][CH2:5][CH2:4][NH:3]2)=[S:27])=[C:18]([F:28])[CH:17]=1

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 12314334Perhydropyridazine hydroiodideHCID 146229544-Chloro-2-fluoro-5-nitrophenylisothiocyanate

생성물 1

HCID 14622955N-(4-chloro-2-fluoro-5-nitrophenylaminothiocarbonyl)perhydropyridazine수율 96%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

반응 조건

온도
-20 °C

실험 절차

To a stirred, cold (-5° C.) solution of 8.56 g (0.0400 mole) of perhydropyridazine hydroiodide in 150 mL of methylene chloride was added dropwise 12.2 g (0.120 mole) of triethylamine. This mixture was stirred for approximately 30 minutes. A solution of 8.0 g (0.034 mole) of 4-chloro-2-fluoro-5-nitrophenylisothiocyanate in methylene chloride was added dropwise to the reaction mixture while maintaining a reaction temperature of -20° C. After complete addition, the reaction mixture was allowed to warm to room temperature and was stirred for two days. The solvent was removed from the mixture by evaporation under reduced pressure leaving a residue. The residue was subjected to column chromatography on silica gel, eluting with ethyl acetate:n-heptane (50:50), to yield 10.4 g of N-[(4-chloro-2-fluoro-5-nitrophenyl)aminothiocarbonyl]perhydropyridazine as a solid, mp 118°-120° C.

후처리

  1. additionAfter complete addition
  2. temperatureto warm to room temperature
  3. stirringwas stirred for two days
  4. customThe solvent was removed from the mixture by evaporation under reduced pressure
  5. customleaving a residue
  6. washeluting with ethyl acetate:n-heptane (50:50)

출처 및 근거

ORD 기록
ord-3063a2a00e5c4d53b3db28b9d051684c
출처 데이터셋
uspto-grants-1990_03
특허 번호
US04906281

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