4-Iodoaniline → alpha-Ethynyl-N-(p-iodophenyl)-benzenemethanamine

HRID 14427

반응식

HRID 14427 반응식
C(=O)([O-])O[CH2:3][CH:4]=[CH:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[I:14][C:15]1[CH:21]=[CH:20][C:18]([NH2:19])=[CH:17][CH:16]=1>>[C:4]([CH:5]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)[NH:19][C:18]1[CH:20]=[CH:21][C:15]([I:14])=[CH:16][CH:17]=1)#[CH:3]

참가 물질

3

반응물 2

HCID 108934-IodoanilineHCID 71446589Cinnamyl carbonate

생성물 1

HCID 86607479alpha-Ethynyl-N-(p-iodophenyl)-benzenemethanamine수율 92.9%

실험 절차

The general procedure was followed with cinnamyl carbonate (0.188 g, 0.979 mmol) and p-iodoaniline (0.220 g, 1.04 mmol). The reaction was conducted at room temperature for 12 h. 1H NMR analysis of the crude reaction mixture indicated the ratio of regioisomers to be 98/2. The mixture was purified by flash column chromatography on silica gel (1.5% ethyl acetate in hexanes) to give the title compound (0.303 g, 92%). HPLC analysis indicated the enantiomeric excess of the product was 96% [Diacel CHIRALCEL OD-H (0.46 cm×25 cm); hexane/2-propanol=99/1; flow rate=0.6 mL/min; detection wavelength=254 nm; TR=18.4 (major), 23.1 (minor) min]: [α]DRT=(c, CHCl3). 1H NMR (400.13 MHz, CDCl3) δ 7.48-7.40 (m, 6H), 7.36 (s, J=4.6 Hz, 1H), 6.43 (dt, J=8.8, 2.4 Hz, 2H), 6.09 (ddd, J=16.8, 10.4, 6.0 Hz, 1H), 5.34 (dt, J=12.0, 1.3 Hz, 1H), 5.31 (dt, J=5.2, 1.2 Hz, 1H), 4.97 (d, J=5.6 Hz, 1H), 4.15 (br s, 1H). 13C NMR (100.59 MHz, CDCl3) δ 146.53, 141.10, 138.35, 137.51, 128.72, 127.53, 126.99, 116.28, 115.69, 78.32, 60.46. Anal. Calcd for C15H14NI: C, 53.75; H, 4.21; N, 4.18; I, 37.86. Found: C, 53.59; H, 4.27; N, 4.17; I, 38.04.

후처리

  1. custom1H NMR analysis of the crude reaction mixture
  2. customThe mixture was purified by flash column chromatography on silica gel (1.5% ethyl acetate in hexanes)

출처 및 근거

ORD 기록
ord-05d85b1fbce346bfbba43531c6bb76d3
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07732365B2

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