Water → 3-nitro-N-(2,2,2-trifluoro-ethyl)-benzenesulfonamide

HRID 2224390노트

반응식

HRID 2224390 반응식
[F:1][C:2]([F:6])([F:5])[CH2:3][NH2:4].[N+:7]([C:10]1[CH:11]=[C:12]([S:16](Cl)(=[O:18])=[O:17])[CH:13]=[CH:14][CH:15]=1)([O-:9])=[O:8].C(N(CC)CC)C.O>O1CCOCC1>[N+:7]([C:10]1[CH:11]=[C:12]([S:16]([NH:4][CH2:3][C:2]([F:6])([F:5])[F:1])(=[O:18])=[O:17])[CH:13]=[CH:14][CH:15]=1)([O-:9])=[O:8]

참가 물질

6

반응물 4

HCID 962WaterHCID 8471TriethylamineHCID 84763-Nitrobenzenesulfonyl chlorideHCID 9773Ethanamine, 2,2,2-trifluoro-

생성물 1

HCID 692881143-nitro-N-(2,2,2-trifluoro-ethyl)-benzenesulfonamide수율 83%

시약·촉매·용매 1

HCID 312751,4-Dioxane용매

실험 절차

To a stirred solution of 2,2,2-trifluoroethylamine (1.17 ml, 15 mmol) in dioxane (37 ml) was added at room temperature 3-nitrobenzenesulfonyl chloride (3.0 g, 14 mmol) and triethylamine (2.06 ml, 15 mmol). The light yellow suspension was stirred at room temperature for 4 h, poured into water (100 ml) and extracted with dichloromethane (3×75 ml). The combined organic layers were washed with water (100 ml) and brine (70 ml), dried (MgSO4) and evaporated. The crude product was further purified by column chromatography on silica gel (heptane/ethyl acetate 1:1) to yield 3-nitro-N-(2,2,2-trifluoro-ethyl)-benzenesulfonamide (3.18 g, 83%) as a light yellow solid. MS (ISP) 283.9 [(M−H)−].

후처리

  1. extractionextracted with dichloromethane (3×75 ml)
  2. washThe combined organic layers were washed with water (100 ml) and brine (70 ml)
  3. dry with materialdried (MgSO4)
  4. customevaporated
  5. customThe crude product was further purified by column chromatography on silica gel (heptane/ethyl acetate 1:1)

출처 및 근거

ORD 기록
ord-fababdeaa52c4851a3df810a4461d813
출처 데이터셋
uspto-grants-2008_05
특허 번호
US07378417B2

반응 노트

불러오는 중…