Diisopropylethylamine → 2-(Trifluoromethyl)-4-[(3,3,3-trifluoropropyl)amino]benzonitrile

HRID 2109107

反応式

HRID 2109107 の反応式
F[C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[C:4]([C:10]([F:13])([F:12])[F:11])[CH:3]=1.Cl.[F:15][C:16]([F:21])([F:20])[CH2:17][CH2:18][NH2:19].CCN(C(C)C)C(C)C>CS(C)=O>[F:11][C:10]([F:13])([F:12])[C:4]1[CH:3]=[C:2]([NH:19][CH2:18][CH2:17][C:16]([F:21])([F:20])[F:15])[CH:9]=[CH:8][C:5]=1[C:6]#[N:7]

参加物

5

反応物 3

HCID 81531DiisopropylethylamineHCID 6050854-Fluoro-2-(trifluoromethyl)benzonitrileHCID 252105053,3,3-Trifluoropropylamine hydrochloride

生成物 1

HCID 576337572-(Trifluoromethyl)-4-[(3,3,3-trifluoropropyl)amino]benzonitrile収率 61%

試薬・触媒・溶媒 1

HCID 679Dimethyl Sulfoxide溶媒

反応条件

温度
200 °C

実験手順

A mixture of 4-fluoro-2-(trifluoromethyl)benzonitrile (0.158 g, 0.84 mmol), (3,3,3-trifluoropropyl)amine hydrochloride (0.125 g, 0.84 mmol) and DIEA (0.326 g, 2.52 mmol) in 1.5 mL of DMSO was heated in a microwave at 200° C. for 20 min. Upon cooling, the mixture was partitioned between Et2O and 0.1N HCl. The organic phase was washed with 0.1N HCl (×2) and brine, dried over Na2SO4 and concentrated. The residue was purified by silica gel chromatography (10-80% EtOAc-hexanes gradient) and the product crystallized from Et2O-hexanes to give 0.144 g (61% yield) of the title compound: 1H NMR (400 MHz, CDCl3) δ 7.60 (d, J=8.6 Hz, 1H), 6.87 (d, J=2.4 Hz, 1H), 6.71 (dd, J=8.6, 2.4 Hz, 1H), 4.56 (bs, NH), 3.53 (q, J=6.5 Hz, 2H), 2.51-2.40 (m, 2H).

後処理

  1. temperatureUpon cooling
  2. customthe mixture was partitioned between Et2O and 0.1N HCl
  3. washThe organic phase was washed with 0.1N HCl (×2) and brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated
  6. customThe residue was purified by silica gel chromatography (10-80% EtOAc-hexanes gradient)
  7. customthe product crystallized from Et2O-hexanes

出典と根拠

ORDレコード
ord-aa12b364963f40a2a4f7b041334ae5a4
出典データセット
uspto-grants-2009_04
特許番号
US07514470B2

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