Acetonitrile → 5-Nitro-2-prop-1-ynyl-phenylamine

HRID 2079912

반응식

HRID 2079912 반응식
Br[C:2]1[CH:8]=[CH:7][C:6]([N+:9]([O-:11])=[O:10])=[CH:5][C:3]=1[NH2:4].C(N([CH2:17][CH3:18])CC)C.[C:19](#N)C>[Cu]I>[N+:9]([C:6]1[CH:7]=[CH:8][C:2]([C:19]#[C:17][CH3:18])=[C:3]([NH2:4])[CH:5]=1)([O-:11])=[O:10]

참가 물질

5

반응물 3

HCID 6342AcetonitrileHCID 8471TriethylamineHCID 826072-Bromo-5-nitroaniline

생성물 1

HCID 671007405-Nitro-2-prop-1-ynyl-phenylamine

시약·촉매·용매 1

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매

실험 절차

Stir a mixture of 2-bromo-5-nitroaniline 16 (2.81 g, 12.95 mmol), dichlorobis(triphenylphospine) palladium (II) (0.45 g, 0.65 mmol), and copper (I) iodide (0.12 g, 0.65 mmol) in anhydrous acetonitrile (10 mL) under inert atmosphere. Saturate the mixture with propyne gas, then add triethyl amine (3.6 mL, 25.90 mmol), seal the vessel, and stir at ambient temperature 14 hours. Concentrate the mixture in vacuo, suspend in 100 mL diethylether, add celite, and filter. Concentrate the filtrate in vacuo and chromatograph the residue over silica gel, eluting with hexanes/ethyl acetate (9:1 v/v) to afford the title compound, 1.75 g (76%). LRMS (API ES+)=177.0 (M+H).

후처리

  1. concentrationSaturate the mixture with propyne gas
  2. stirringstir at ambient temperature 14 hours
  3. concentrationConcentrate the mixture in vacuo
  4. additionadd celite
  5. filtrationfilter
  6. concentrationConcentrate the filtrate in vacuo and chromatograph the residue over silica gel
  7. washeluting with hexanes/ethyl acetate (9:1 v/v)

출처 및 근거

ORD 기록
ord-1ff459fe65ad4018aea050ce3b4c0d14
출처 데이터셋
uspto-grants-2011_04
특허 번호
US07932284B2

연결된 노트

불러오는 중…