Tetrahydrofuran → N1-(4-(3-bromopropoxy)phenyl)-N1,N4,N4-tris(4-methoxyphenyl)benzene-1,4-diamine

HRID 2041851노트

반응식

HRID 2041851 반응식
CS(O[CH2:6][CH2:7][CH2:8][O:9][C:10]1[CH:15]=[CH:14][C:13]([N:16]([C:25]2[CH:30]=[CH:29][C:28]([N:31]([C:40]3[CH:45]=[CH:44][C:43]([O:46][CH3:47])=[CH:42][CH:41]=3)[C:32]3[CH:37]=[CH:36][C:35]([O:38][CH3:39])=[CH:34][CH:33]=3)=[CH:27][CH:26]=2)[C:17]2[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][CH:18]=2)=[CH:12][CH:11]=1)(=O)=O.[Br-:48].[Li+].O1CCCC1>O>[Br:48][CH2:6][CH2:7][CH2:8][O:9][C:10]1[CH:15]=[CH:14][C:13]([N:16]([C:17]2[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][CH:18]=2)[C:25]2[CH:30]=[CH:29][C:28]([N:31]([C:40]3[CH:45]=[CH:44][C:43]([O:46][CH3:47])=[CH:42][CH:41]=3)[C:32]3[CH:37]=[CH:36][C:35]([O:38][CH3:39])=[CH:34][CH:33]=3)=[CH:27][CH:26]=2)=[CH:12][CH:11]=1

참가 물질

5

반응물 3

HCID 8028TetrahydrofuranHCID 82050Lithium BromideHCID 86653413HCID 86653413, 화합물

생성물 1

HCID 67159998N1-(4-(3-bromopropoxy)phenyl)-N1,N4,N4-tris(4-methoxyphenyl)benzene-1,4-diamine

시약·촉매·용매 1

HCID 962Water용매

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온도
60 °C

실험 절차

To a dry schlenk flask was added 3-(4-((4-(bis(4-methoxyphenyl)amino)phenyl)(4-methoxyphenyl)amino)phenoxy)propyl methanesulfonate (4.06 g, 6.20 mmol). The flask was evacuated under vacuum and filled with nitrogen. Lithium bromide (5.39 g; 62.0 mmol) and tetrahydrofuran (6.2 mL) were added under nitrogen. The mixture was allowed to stir at 60° C. overnight. Upon disappearance of the starting material the reaction mixture was poured into a separatory funnel containing 100 mL of cold water. The product was extracted using 3×50 mL ether. The organic layers were combined and washed with 3×50 mL of water. The resulting ether layers were dried over Na2SO4. The drying agent was removed by filtration and the solvent was removed under reduced pressure. The residual solvent was removed in vacuo (3.12 g, 78.2%). 1H NMR (400 MHz, C3D6O) δ 6.97 (m, 8H), 6.86 (m, 8H), 6.80 (s, 4H), 4.09 (t, J=5.9 Hz, 2H), 3.75 (s, 9H), 3.66 (t, J=6.6 Hz, 2H), 2.28 (q, J=6.2 Hz, 2H). 13C{1H} NMR (400 MHz, C3D6O) δ 156.39, 155.34, 143.71, 143.51, 142.22, 127.05, 126.27, 126.03, 123.90, 123.70, 116.10, 115.40, 114.61, 66.34, 55.62, 33.25, 31.05. HRMS-EI (m/z): [M]+ calcd for C36H35BrN2O4, 640.18; found, 640.1). Anal. Calcd for C36H35BrN2O4: C, 67.60; H, 5.52; N, 4.38. Found: C, 67.43; H, 5.61; N, 4.24.

후처리

  1. customThe flask was evacuated under vacuum
  2. additionfilled with nitrogen
  3. additionUpon disappearance of the starting material the reaction mixture was poured into a separatory funnel
  4. extractionThe product was extracted
  5. washwashed with 3×50 mL of water
  6. dry with materialThe resulting ether layers were dried over Na2SO4
  7. customThe drying agent was removed by filtration
  8. customthe solvent was removed under reduced pressure
  9. customThe residual solvent was removed in vacuo (3.12 g, 78.2%)

출처 및 근거

ORD 기록
ord-f9c3a5459d7a4a359e61b14810262042
출처 데이터셋
uspto-grants-2013_11
특허 번호
US08586208B2

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