Sodium hydride → 4-([N-Ethyl-N-phenyl-2-aminoethyl]oxymethyl)benzophenone

HRID 47173

반응식

HRID 47173 반응식
[CH2:1]([N:3]([CH2:10][CH2:11][OH:12])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)[CH3:2].[H-].[Na+].Br[CH2:16][C:17]1[CH:30]=[CH:29][C:20]([C:21]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=[O:22])=[CH:19][CH:18]=1>C1COCC1>[CH2:1]([N:3]([C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1)[CH2:10][CH2:11][O:12][CH2:16][C:17]1[CH:30]=[CH:29][C:20]([C:21]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=[O:22])=[CH:19][CH:18]=1)[CH3:2]

참가 물질

5

반응물 3

HCID 24758Sodium hydrideHCID 623382-(N-ethylanilino)ethanolHCID 1229514-(Bromomethyl)benzophenone

생성물 1

HCID 221775034-([N-Ethyl-N-phenyl-2-aminoethyl]oxymethyl)benzophenone수율 80%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
20 °C

실험 절차

2-(N-Ethylanilino)ethanol (3.03 g, 18.4 mmol, 1.2 eq) in THF (20 cm3) was treated with NaH (60% dispersion in oil, 524 mg, 13,1 mmol, 1.4 eq) and stirred at 20° C. for 1 hour. 4-Bromomethylbenzophenone (4.21 g, 15.3 mmol) was then added and stirring continued for 72 hours. Excess solvent was removed in vacuo and the residue diluted with DCM, washed with water and NaHCO3 solution (sat.), dried (MgSO4) and solvent removed under vacuum. The resulting oil was purified by flash chromatography, eluting with petroleum (bp 40-60° C.):EtOAc (9:1), to give the desired product as a yellow oil (4.36 g, 80%), Rf=0.54 (4:1, petrol:EtOAc) (Found: C, 78.34; H, 6.86; N, 5.29. C24H25NO2 requires C, 80.19; H, 7.01; N, 3.90%); νmax (film/cm−1 1658 (s), 1598 (s), 1506 (s); δH (200 MHz; CDCl3) 1.22 (3H, t, J 7, CH3), 3.49 (2H, q, J 7, CH2CH3), 3.58-3.79 (4H, m, OCH2CH2N), 4.66 (2H, s, ArCH2O), 6.69-6.79 (3H, m, ArH o- and p- to NR2), 7.28 (2H, dd, J 7, 7, ArH m- to NR2), 7.46-7.68 (5H, m, ArH), 7.80-7.88 (4H, m, ArH o- to C═O), δC (50.3 MHz; CDCl3) 12.2 (CH3), 45.5 (NCH2CH3), 50.1 (NCH2CH2O), 68.5 (NCH2CH2O), 72.2 (ArCH2O), 111.8 (ArCH o- to NR2), 115.8 (ArCH p- to NR2), 127.0, 128.3, 129.3, 130.0 and 130.3 (ArCH o- and m- to C═O and ArCH m- to NR2), 132.4 (ArCH p- to C═O), 136.8 and 137.7 (4° ArCC═O), 143.2 (4° ArCCH2O), 147.7 (4° ArCNR2), 196.4 (C═O); m/z (APCI+) 360 ([M+H]+, 30%); HRMS C24H26O2N requires 360.1963; found 360.1963.

후처리

  1. stirringstirring
  2. waitcontinued for 72 hours
  3. customExcess solvent was removed in vacuo
  4. additionthe residue diluted with DCM
  5. washwashed with water and NaHCO3 solution (sat.)
  6. dry with materialdried (MgSO4) and solvent
  7. customremoved under vacuum
  8. customThe resulting oil was purified by flash chromatography
  9. washeluting with petroleum (bp 40-60° C.)

출처 및 근거

ORD 기록
ord-23461bdad4054a56a320bb8926e582fc
출처 데이터셋
uspto-grants-2004_03
특허 번호
US06699527B1

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