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2-Iodo-4-nitroaniline → HCID 53741589, 화합물

HRID 1769636
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HRID 1769636 반응식
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]
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참가 물질

8

반응물 4

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

생성물 1

HCID 53741589HCID 53741589, 화합물수율 42.4%

시약·촉매·용매 3

HCID 167845
palladium(II) acetate
촉매
HCID 3283Diethyl Ether용매
HCID 6228Dimethylformamide용매

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온도
70 °C

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-46cbe4e017f2451bbba70f566988022a
출처 데이터셋
uspto-grants-1995_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05382592

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