Triethylamine → Diethyl 2-(3-(3-(2,6-dichlorophenyl)isoxazol-5-yl)phenylamino)ethylphosphonate

HRID 1782176노트

반응식

HRID 1782176 반응식
[Cl:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]([Cl:12])[C:3]=1[C:4](Cl)=[N:5][OH:6].[C:13]([C:15]1[CH:16]=[C:17]([NH:21][CH2:22][CH2:23][P:24](=[O:31])([O:28][CH2:29][CH3:30])[O:25][CH2:26][CH3:27])[CH:18]=[CH:19][CH:20]=1)#[CH:14].C(N(CC)CC)C>O1CCCC1>[Cl:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]([Cl:12])[C:3]=1[C:4]1[CH:14]=[C:13]([C:15]2[CH:16]=[C:17]([NH:21][CH2:22][CH2:23][P:24](=[O:31])([O:28][CH2:29][CH3:30])[O:25][CH2:26][CH3:27])[CH:18]=[CH:19][CH:20]=2)[O:6][N:5]=1

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 28001642,6-DichlorobenzaldchloroximeHCID 57588428Diethyl 2-(3-ethynylphenylamino)ethylphosphonate

생성물 1

HCID 57588335Diethyl 2-(3-(3-(2,6-dichlorophenyl)isoxazol-5-yl)phenylamino)ethylphosphonate수율 89.2%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

2,6-Dichloro-N-hydroxybenzimidoyl chloride (370 mg, 1.6 mmol) and diethyl 2-(3-ethynylphenylamino)ethylphosphonate (450 mg, 1.6 mmol) were dissolved in anhydrous tetrahydrofuran (40 mL) and triethylamine (0.30 mL, 1.6 mmol). The mixture was then heated at reflux for 5 h. The reaction was cooled to room temperature and the solvent was removed under reduced pressure. The residue was dissolved in ethyl acetate and washed successively with water and brine. The ethyl acetate solution was dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The resulting solid was purified by flash column chromatography on silica gel, eluting with 98:2 methylene chloride:methanol to give diethyl 2-(3-(3-(2,6-dichlorophenyl)isoxazol-5-yl)phenylamino)ethylphosphonate (670 mg) as a pale yellow oil. 1H NMR (CDCl3): 7.30 (m, 2H), 7.21 (m, 1H), 7.15 (m, 1H), 7.05 (m, 1H), 7.00 (m, 1H), 6.59 (m, 1H), 6.48 (s, 1H), 4.03 (m, 4H), 3.40 (m, 2H), 2.00 (m, 2H), 1.24 ppm (m, 6H). MW=469 confirmed by LC-MS, tr=14.80 min (Method Y) MH+=467-472.

후처리

  1. temperatureThe mixture was then heated
  2. temperatureat reflux for 5 h
  3. customthe solvent was removed under reduced pressure
  4. dissolutionThe residue was dissolved in ethyl acetate
  5. washwashed successively with water and brine
  6. dry with materialThe ethyl acetate solution was dried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customThe resulting solid was purified by flash column chromatography on silica gel
  10. washeluting with 98:2 methylene chloride

출처 및 근거

ORD 기록
ord-6f1d4e2fd773458f8602059d2230dd49
출처 데이터셋
uspto-grants-2009_03
특허 번호
US07498353B2

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