Carbon Tetrachloride → HCID 11198434、化合物

HRID 2109102ノート

反応式

HRID 2109102 の反応式
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([N:9]([CH2:16][C:17]([F:20])([F:19])[F:18])[CH2:10][CH:11]([CH3:15])[C:12]([NH2:14])=O)=[CH:5][C:4]=1[C:21]([F:24])([F:23])[F:22])#[N:2].C(Cl)(Cl)(Cl)Cl.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>ClCCCl>[C:12]([CH:11]([CH3:15])[CH2:10][N:9]([CH2:16][C:17]([F:18])([F:19])[F:20])[C:6]1[CH:7]=[CH:8][C:3]([C:1]#[N:2])=[C:4]([C:21]([F:22])([F:24])[F:23])[CH:5]=1)#[N:14]

参加物

5

反応物 3

HCID 5943Carbon TetrachlorideHCID 11776TriphenylphosphineHCID 57633767HCID 57633767、化合物

生成物 1

HCID 11198434HCID 11198434、化合物収率 52.2%

試薬・触媒・溶媒 1

HCID 111,2-Dichloroethane溶媒

反応条件

温度
87 °C

実験手順

A mixture of 3-[[4-cyano-3-(trifluoromethyl)phenyl](2,2,2-trifluoroethyl)amino]-2-methylpropanamide (0.044 mg, 0.12 mmol), CCl4 (1.5 mL), DCE (1.5 mL) and polymer-supported triphenyl phosphine (3 mmol/g, 0.089 g, 0.27 mmol) was heated at 87° C. for 2 h. Upon cooling, the resin was filtered off, washed thoroughly with CHCl3 and the filtrate concentrated in vacuo. The residue was purified by silica gel chromatography (5-40% EtOAc-hexane gradient) and the product crystallized from CH2Cl2-hexanes to give the title compound as a white solid (0.021 g, 52% yield): 1H NMR (400 MHz, CDCl3) δ 7.72 (d, J=8.8 Hz, 1H), 7.03 (d, J=2.6 Hz, 1H), 6.94 (dd, J=8.8, 2.6 Hz, 1H), 4.31-4.10 (m, 2H), 3.79-3.68 (m, 2H), 3.10-3.01 (m, 1H), 1.41 (d, J=7.2 Hz, 3H); MS (ES) m/z 336 (M+1).

後処理

  1. temperatureUpon cooling
  2. filtrationthe resin was filtered off
  3. washwashed thoroughly with CHCl3
  4. concentrationthe filtrate concentrated in vacuo
  5. customThe residue was purified by silica gel chromatography (5-40% EtOAc-hexane gradient)
  6. customthe product crystallized from CH2Cl2-hexanes

出典と根拠

ORDレコード
ord-5ad4494f47ee4fc1bcbb9414bbf8b70f
出典データセット
uspto-grants-2009_04
特許番号
US07514470B2

反応ノート

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