ホームMCPワークベンチSkills
ホームワークベンチ通知マイページ
llms.txt · MCPガイドプライバシーポリシー · 利用規約 · サポートv1.8.0
  1. ホーム
  2. /反応

2-Iodo-4-nitroaniline → HCID 53741589、化合物

HRID 1769636
ノート
印刷プレビュー

反応式

HRID 1769636 の反応式
I[C:2]1[CH:8]=[C:7]([N+:9]([O-:11])=[O:10])[CH:6]=[CH:5][C:3]=1[NH2:4].[CH3:12][Si:13]([CH3:27])([CH3:26])[C:14]#[C:15][CH2:16][CH2:17][O:18][Si:19]([C:22]([CH3:25])([CH3:24])[CH3:23])([CH3:21])[CH3:20].C([O-])(=O)C.[K+].[Cl-].[Li+]>CN(C=O)C.CCOCC.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[N+:9]([C:7]1[CH:8]=[C:2]2[C:3](=[CH:5][CH:6]=1)[NH:4][C:14]([Si:13]([CH3:12])([CH3:27])[CH3:26])=[C:15]2[CH2:16][CH2:17][O:18][Si:19]([C:22]([CH3:25])([CH3:24])[CH3:23])([CH3:20])[CH3:21])([O-:11])=[O:10]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

8

反応物 4

HCID 2226292-Iodo-4-nitroanilineHCID 433294Lithium ChlorideHCID 517044Potassium AcetateHCID 13679439tert-Butyl(dimethyl){[4-(trimethylsilyl)but-3-yn-1-yl]oxy}silane

生成物 1

HCID 53741589HCID 53741589、化合物収率 42.4%

試薬・触媒・溶媒 3

HCID 167845
palladium(II) acetate
触媒
HCID 3283Diethyl Ether溶媒
HCID 6228Dimethylformamide溶媒

反応条件

温度
70 °C

実験手順

A mixture of 2-iodo-4-nitroaniline (7.92 g, 0.030 mol), 1-(trimethylsilyl)-4-(t-butyldimethylsiloxy)-1-butyne (15.36 g, 0.060 mol), potassium acetate (14.70 g, 0.15 mol), lithium chloride (1.27 g, 0.030 mol) and palladium (II) acetate (0.675 g, 0.003 mol) in 100 mL of dry DMF was heated at 70° C. (oil-bath temperature) under Ar for 2.5 h. The cooled reaction mixture was diluted with ether and the aqueous phase was separated and extracted with ethyl acetate. The combined organic phases were washed (H2O, brine), dried (Na2SO4) and evaporated. The resulting residue was chromatographed (SiO2 /hexane-ethyl acetate, 4:1) to give a dark orange solid which was rechromatographed (SiO2 /hexane-CH2Cl2, 4:1 to 6:4) to give the title compound (5.00 g, 42%) as a yellow solid: IR (neat) 3414, 1328, 1253, 845 cm-1 ; 1H NMR (CDCl3, 200 MHz) δ 8.63 (d, J=2.2 Hz, 1H), 8.21 (br s, 1H), 8.09 (dd, J=9.0, 2.2 Hz, 1H), 7.35 (d, J=9.0 Hz, 1H), 3.84 (t, J=7.2 Hz, 2H), 3.09 (t, J=7.2 Hz, 2H), 0.85 (s, 9H), 0.42 (s, 9H), -0.01 (s, 6H).

後処理

  1. customThe cooled reaction mixture
  2. customthe aqueous phase was separated
  3. extractionextracted with ethyl acetate
  4. washThe combined organic phases were washed (H2O, brine)
  5. dry with materialdried (Na2SO4)
  6. customevaporated
  7. customThe resulting residue was chromatographed (SiO2 /hexane-ethyl acetate, 4:1)
  8. customto give a dark orange solid which
  9. customwas rechromatographed (SiO2 /hexane-CH2Cl2, 4:1 to 6:4)

出典と根拠

ORDレコード
ord-46cbe4e017f2451bbba70f566988022a
出典データセット
uspto-grants-1995_01
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05382592

反応ノート

読み込み中…

このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート