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

HRID 1944271

反応式

HRID 1944271 の反応式
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]

参加物

8

反応物 5

HCID 947NitrogenHCID 74233-NitroanilineHCID 8471TriethylamineHCID 648603,4,5-Trimethoxyhydrocinnamic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

生成物 1

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

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒HCID 6344Dichloromethane溶媒

実験手順

(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. NH2Cl 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 60PF, 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=8.01 Hz); 8.31 (s, 1H).

後処理

  1. custom(The following reaction
  2. customQuench
  3. customreaction solution with sat. aqu
  4. customNH2Cl 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 60PF, EtOAc/CyH 1+1)

出典と根拠

ORDレコード
ord-5df01ceae3134ce2a7304b43d3ec6deb
出典データセット
uspto-grants-2013_03
特許番号
US08394835B2

関連ノート

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