Triethylamine → N-cyclopropyl-4-methyl-3-nitrobenzamide

HRID 403027

Reaktionsgleichung

Reaktionsgleichung von HRID 403027
[CH3:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](Cl)=[O:7])=[CH:4][C:3]=1[N+:11]([O-:13])=[O:12].[CH:14]1([NH2:17])[CH2:16][CH2:15]1.C(N(CC)CC)C>C(Cl)Cl>[CH:14]1([NH:17][C:6](=[O:7])[C:5]2[CH:9]=[CH:10][C:2]([CH3:1])=[C:3]([N+:11]([O-:13])=[O:12])[CH:4]=2)[CH2:16][CH2:15]1

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 663234-Methyl-3-nitrobenzoyl chlorideHCID 69828Cyclopropylamine

Produkt 1

HCID 2162665N-cyclopropyl-4-methyl-3-nitrobenzamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a stirred solution of 4-methyl-3 nitrobenzoyl chloride (20 g) in methylene chloride (200 mL) at 0° C. was added a mixture of cyclopropylamine (7.62 mL) and triethylamine (28 mL). The mixture was allowed to warm to room temperature and stirred for a further 16 hours. The reaction mixture was evaporated in vacuo and a saturated aqueous solution of sodium bicarbonate was added. The precipitated solid was filtered off and washed with isohexane and dried (magnesium sulphate) to give N-cyclopropyl-4-methyl-3-nitrobenzamide as a colourless solid (22.9 g); NMR Spectrum: (DMSOd6) 0.60 (m, 2H), 0.72 (m, 2H), 2.56 (s, 3H), 2.87 (m, 1H), 7.60 (d, 1H), 8.06 (m, 1H), 8.41 (d, 1H), 8.67 (d, 1H); Mass Spectrum: M+H+ 221. B) A suspension of N-cyclopropyl-4-methyl-3-nitrobenzamide (22.92 g) and 10% palladium on carbon (2 g) in absolute alcohol (500 mL) was agitated under a hydrogen atmosphere for 16 hours. The reaction mixture was filtered through diatomaceous earth (Celite®) and the filtrate evaporated to dryness to give the title compound as a colourless solid (17.1 g); NMR Spectrum: (DMSOd6) 0.53 (m, 2H), 0.65 (m, 2H), 2.07 (s, 3H), 2.80 (m, 1H), 6.92 (m, 2H), 7.06 (d, 1H), 8.09 (d, 1H); Mass Spectrum: M+H+ 191.

Aufarbeitung

  1. customThe reaction mixture was evaporated in vacuo
  2. additiona saturated aqueous solution of sodium bicarbonate was added
  3. filtrationThe precipitated solid was filtered off
  4. washwashed with isohexane
  5. dry with materialdried (magnesium sulphate)

Quellen und Nachweise

ORD-Eintrag
ord-5f1ad78a699c4efa86e6b8cf0d7e3724
Quelldatensatz
uspto-grants-2014_06
Patentnummer
US08742124B2

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