Triethylamine → N-(2,2-diethoxyethyl)-3-methoxy-2-nitrobenzamide

HRID 577486

Reaktionsgleichung

Reaktionsgleichung von HRID 577486
C(Cl)(=O)C(Cl)=O.[CH3:7][O:8][C:9]1[C:10]([N+:18]([O-:20])=[O:19])=[C:11]([CH:15]=[CH:16][CH:17]=1)[C:12]([OH:14])=O.[CH2:21]([O:23][CH:24]([O:27][CH2:28][CH3:29])[CH2:25][NH2:26])[CH3:22].C(N(CC)CC)C>ClCCl.CN(C)C=O>[CH2:21]([O:23][CH:24]([O:27][CH2:28][CH3:29])[CH2:25][NH:26][C:12](=[O:14])[C:11]1[CH:15]=[CH:16][CH:17]=[C:9]([O:8][CH3:7])[C:10]=1[N+:18]([O-:20])=[O:19])[CH3:22]

Komponenten

7

Edukt 4

HCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 695242,2-DiethoxyethylamineHCID 786323-Methoxy-2-nitrobenzoic acid

Produkt 1

HCID 86723712N-(2,2-diethoxyethyl)-3-methoxy-2-nitrobenzamideAusbeute 97 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideKatalysatorHCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

Oxalyl chloride (34 mL, 0.395 mol) was added to a solution of 3-methoxy-2-nitrobenzoic acid (60 g, 0.305 mol) in dry dichloromethane (600 mL), followed by N,N-dimethylformamide (0.6 mL, 7.8 mmol), which initiates mild gas evolution. The mixture was stirred at room temperature for two hours, then concentrated under vacuum to remove volatiles. The crude acid chloride was dissolved in dry dichloromethane (150 mL) then added dropwise to a cooled (5° C.) solution of aminoacetaldehyde diethylacetal (48 mL, 0.33 mol) and triethylamine (52 mL, 0.374 mol) in dry dichloromethane (250 mL). The mixture was stirred at room temperature for two hours, then washed with saturated aqueous sodium bicarbonate (2×100 mL) and brine (100 mL). The organics were dried over sodium sulfate and concentrated to give N-(2,2-diethoxyethyl)-3-methoxy-2-nitrobenzamide (296a, 92 g, 97% yield) as a yellow solid. MS: 335 [M+1].

Aufarbeitung

  1. concentrationconcentrated under vacuum
  2. customto remove volatiles
  3. dissolutionThe crude acid chloride was dissolved in dry dichloromethane (150 mL)
  4. additionthen added dropwise to
  5. stirringThe mixture was stirred at room temperature for two hours
  6. washwashed with saturated aqueous sodium bicarbonate (2×100 mL) and brine (100 mL)
  7. dry with materialThe organics were dried over sodium sulfate
  8. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-3dd1029fa0c342ca8dc5e1dce0bb5721
Quelldatensatz
uspto-grants-2015_05
Patentnummer
US09040515B2

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