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

HRID 2079912

反応式

HRID 2079912 の反応式
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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

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

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-1ff459fe65ad4018aea050ce3b4c0d14
出典データセット
uspto-grants-2011_04
特許番号
US07932284B2

関連ノート

読み込み中…