氮 → N-(3-Nitro-phenyl)-3-(3,4,5-trimethoxy-phenyl)-propionamide

HRID 2075942

反应方程式

HRID 2075942 反应方程式
N#N.CCN=C=NCCCN(C)C.Cl.CCN(CC)CC.[CH3:22][O:23][C:24]1[CH:25]=[C:26]([CH2:34][CH2:35][C:36]([OH:38])=O)[CH:27]=[C:28]([O:32][CH3:33])[C:29]=1[O:30][CH3:31].[N+:39]([C:42]1[CH:43]=[C:44]([NH2:48])[CH:45]=[CH:46][CH:47]=1)([O-:41])=[O:40]>ClCCl.CN(C1C=CN=CC=1)C>[N+:39]([C:42]1[CH:43]=[C:44]([NH:48][C:36](=[O:38])[CH2:35][CH2:34][C:26]2[CH:27]=[C:28]([O:32][CH3:33])[C:29]([O:30][CH3:31])=[C:24]([O:23][CH3:22])[CH:25]=2)[CH:45]=[CH:46][CH:47]=1)([O-:41])=[O:40]

参与物

8

反应物 5

HCID 947氮HCID 74233-硝基苯胺HCID 8471三乙胺HCID 648603-(3,4,5-三甲氧基苯基)丙酸HCID 27239391-乙基-(3-二甲基氨基丙基)碳酰二亚胺盐酸盐

产物 1

HCID 9411047N-(3-Nitro-phenyl)-3-(3,4,5-trimethoxy-phenyl)-propionamide收率 70.5%

试剂、催化剂与溶剂 2

HCID 142844-二甲氨基吡啶(DMAP)催化剂HCID 6344二氯甲烷溶剂

实验过程

(The following reaction is done in an anhydrous N2 atmosphere.) Suspend EDC hydrochloride (402 mg, 2.10 mmol) and Et3N (293 μL, 2.10 mmol) in anhydrous dichloromethane (17.0 mL) and stir the resulting solution for 5 min at rt. Add 3-(3,4,5-trimethoxy-phenyl)-propionic acid (481 mg, 2.00 mmol) and DMAP (24 mg, 0.20 mmol) and stir the resulting solution for 5 min. Add 3-nitro-phenylamine (90) (414 mg, 3.00 mmol) and stir the reaction solution 24 h at rt. Quench reaction solution with sat. aqu. NH4Cl and water, separate layers and extract aqu. layer with EtOAc (3 times). Wash the combined organic layer with water and brine and dry with Na2SO4. Purify the crude product by preparative radial chromatography (silica gel 60 PF, EtOAc/CyH 1+1) to obtain N-(3-nitro-phenyl)-3-(3,4,5-trimethoxy-phenyl)-propionamide (91) (508 mg, 70%) as a yellowish solid. 1H NMR (400 MHz, CDCl3): 2.65 (t, 2H, J=7.3 Hz); 2.98 (t, 2H, J=7.3 Hz); 3.79 (s, 6H); 3.81 (s, 3H), 6.42 (s, 2H); 7.41 (s, 1H); 7.45 (t, 1H, J=8.0 Hz); 7.84 (d, 1H, J=8.0 Hz); 7.92 (d, 1H, J=8.0 Hz); 8.31 (s, 1H).

后处理

  1. custom(The following reaction
  2. customQuench
  3. customreaction solution with sat. aqu
  4. customNH4Cl and water, separate layers
  5. extractionextract aqu
  6. washWash the combined organic layer with water and brine
  7. dry with materialdry with Na2SO4
  8. customPurify the crude product by preparative radial chromatography (silica gel 60 PF, EtOAc/CyH 1+1)

来源与证据

ORD记录
ord-6573d147a3de4e2993faaf4c262d7a43
来源数据集
uspto-grants-2011_04
专利号
US07923473B2

关联笔记

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