Carbon Tetrachloride → HCID 11198434, 화합물

HRID 2109102노트

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HRID 2109102 반응식
[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]

참가 물질

5

반응물 3

HCID 5943Carbon TetrachlorideHCID 11776TriphenylphosphineHCID 57633767HCID 57633767, 화합물

생성물 1

HCID 11198434HCID 11198434, 화합물수율 52.2%

시약·촉매·용매 1

HCID 111,2-Dichloroethane용매

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온도
87 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-5ad4494f47ee4fc1bcbb9414bbf8b70f
출처 데이터셋
uspto-grants-2009_04
특허 번호
US07514470B2

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