Triethylamine → HCID 57824451, 화합물

HRID 1470819

반응식

HRID 1470819 반응식
ClN1C(=O)CCC1=O.[F:9][C:10]([F:22])([F:21])[O:11][C:12]1[CH:20]=[CH:19][C:15]([CH:16]=[N:17][OH:18])=[CH:14][CH:13]=1.[NH2:23][C:24]1[CH:31]=[CH:30][C:27]([CH:28]=[CH2:29])=[CH:26][CH:25]=1.C(N(CC)CC)C>C(Cl)(Cl)Cl.N1C=CC=CC=1>[F:9][C:10]([F:21])([F:22])[O:11][C:12]1[CH:20]=[CH:19][C:15]([C:16]2[CH2:29][CH:28]([C:27]3[CH:30]=[CH:31][C:24]([NH2:23])=[CH:25][CH:26]=3)[O:18][N:17]=2)=[CH:14][CH:13]=1

참가 물질

7

반응물 4

HCID 8471TriethylamineHCID 31398ChlorosuccinimideHCID 737004-AminostyreneHCID 2777199p-Trifluoromethoxybenzaldehyde oxime

생성물 1

HCID 57824451HCID 57824451, 화합물수율 61.2%

시약·촉매·용매 2

HCID 1049Pyridine용매HCID 6212Chloroform용매3회

반응 조건

온도
50 °C

실험 절차

To a stirred solution of N-chlorosuccinimide (0.634 mmol, 85 μL) and pyridine (4 μL) in 2.5 mL of chloroform was added p-trifluoromethoxybenzaldehyde oxime (130 mg, 0.634 mmol). The reaction was heated at 50° C. for 3 h. 4-Aminostyrene (0.793 mmol, 93 μL) was then added followed by a solution of triethylamine (0.666 mmol, 93 μL) dissolved in 0.5 mL of CHCl3 dropwise. The reaction was stirred at 50° C. for 3 h. The cooled solution was diluted with chloroform (15 mL) and washed with water (2×10 mL). The organic phase was then dried over MgSO4, filtered and concentrated. The residue was purified via radial chromatography using a 2:1 hexane/EtOAc solution as the eluent (Rf=0.18) to afford 4-[3-(4-trifluoromethoxyphenyl)-4,5-dihydro-isoxazol-5-yl]-phenylamine (125 mg; 61%). 1H NMR (400 MHz, CDCl3) δ 7.73 (d, J=8.2 Hz, 2H), 7.25 (d, J=8.2 Hz, 2H), 7.17 (d, J=8.2 Hz, 2H), 6.68 (d, J=8.2 Hz, 2H), 5.65 (dd, J=10.9, 8.9 Hz, 1H), 3.55-3.75 (bs, 2H), 3.67 (dd, J=16.8, 10.9 Hz, 1H), 3.30 (dd, J=16.8, 8.9 Hz, 1H); EIMS 322 (M+).

후처리

  1. washwashed with water (2×10 mL)
  2. dry with materialThe organic phase was then dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue was purified via radial chromatography

출처 및 근거

ORD 기록
ord-4577daa79dc54cf0be8c11f5d3237802
출처 데이터셋
uspto-grants-2015_04
특허 번호
US09006468B2

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