Pyridine → N-(3-nitro-4-methylphenyl)-3-morpholinobenzamide

HRID 2302252Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2302252
[O:1]1[CH2:6][CH2:5][N:4]([C:7]2[CH:8]=[C:9]([CH:13]=[CH:14][CH:15]=2)[C:10](Cl)=[O:11])[CH2:3][CH2:2]1.[CH3:16][C:17]1[CH:23]=[CH:22][C:20]([NH2:21])=[CH:19][C:18]=1[N+:24]([O-:26])=[O:25].N1C=CC=CC=1>C(Cl)Cl>[N+:24]([C:18]1[CH:19]=[C:20]([NH:21][C:10](=[O:11])[C:9]2[CH:13]=[CH:14][CH:15]=[C:7]([N:4]3[CH2:5][CH2:6][O:1][CH2:2][CH2:3]3)[CH:8]=2)[CH:22]=[CH:23][C:17]=1[CH3:16])([O-:26])=[O:25]

Komponenten

5

Edukt 3

HCID 1049PyridineHCID 83904-Methyl-3-nitroanilineHCID 220579723-Morpholinobenzoyl chloride

Produkt 1

HCID 22057949N-(3-nitro-4-methylphenyl)-3-morpholinobenzamideAusbeute 83,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

A solution of 3-morpholinobenzoyl chloride (0.24 g) in methylene chloride (5 ml) was added to a stirred mixture of 4-methyl-3-nitroaniline (0.15 g), pyridine (0.24 ml) and methylene chloride (10 ml). The reaction mixture was stirred at ambient temperature for 16 hours. The organic phase was washed with water and with a saturated aqueous sodium bicarbonate solution. The organic layer was dried (MgSO4) and evaporated. The residual solid was triturated under diethyl ether and the resultant solid was isolated and dried to give N-(3-nitro-4-methylphenyl)-3-morpholinobenzamide (0.28 g); NMR Spectrum: (DMSOd6) 3.2 (t, 4H), 3.3 (s, 3H), 3.78 (t, 4H), 7.19 (s, 1H), 7.4 (m, 2H), 7.47 (d, 2H). 8.0 (d, 1H), 8.83 (s, 1H), 10.23 (s, 1H).

Aufarbeitung

  1. washThe organic phase was washed with water and with a saturated aqueous sodium bicarbonate solution
  2. dry with materialThe organic layer was dried (MgSO4)
  3. customevaporated
  4. customThe residual solid was triturated under diethyl ether
  5. customthe resultant solid was isolated
  6. customdried

Quellen und Nachweise

ORD-Eintrag
ord-dd2a273aea67408a9d363f7379513b49
Quelldatensatz
uspto-grants-2002_08
Patentnummer
US06432949B1

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