2,6-Di-tert-butyl-4-methylphenol → 2-Methyl-N-(3-methyl-4-nitrophenyl)oxirane-2-carboxamide

HRID 133730Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 133730
ClC1C=C(C=CC=1)C(OO)=[O:6].[CH3:12][C:13](=[CH2:27])[C:14]([NH:16][C:17]1[CH:22]=[CH:21][C:20]([N+:23]([O-:25])=[O:24])=[C:19]([CH3:26])[CH:18]=1)=[O:15].C(C1C=C(C)C=C(C(C)(C)C)C=1O)(C)(C)C>ClCCCl>[CH3:26][C:19]1[CH:18]=[C:17]([NH:16][C:14]([C:13]2([CH3:12])[CH2:27][O:6]2)=[O:15])[CH:22]=[CH:21][C:20]=1[N+:23]([O-:25])=[O:24]

Komponenten

5

Edukt 3

HCID 314042,6-Di-tert-butyl-4-methylphenolHCID 70297m-Chloroperbenzoic acidHCID 450976432-Methyl-N-(3-methyl-4-nitrophenyl)acrylamide

Produkt 1

HCID 714200032-Methyl-N-(3-methyl-4-nitrophenyl)oxirane-2-carboxamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 111,2-DichloroethaneLösungsmittel

Versuchsvorschrift

m-Chloroperoxybenzoic acid (6.7 g, 29.9 mmol) was added in portions at 60° C. to a solution of 2-methyl-N-(3-methyl-4-nitrophenyl)acrylamide (2.9 g, 13.2 mmol) and 2,6-di-tert-butyl-4-methylphenol (66 mg) in 1,2-dichloroethane (80 ml). The string was continued at 60° C. for 6 h, and the reaction mixture was allowed to cool to room temperature. The precipitated m-chlorobenzoic acid was filtered, and the filtrate was extracted with 1 M Na2CO3 (4×60 ml). The organic phase was dried over Na2SO4 and evaporated. The yield was 3.05 g. 1H NMR (DMSO-d6): 1.54 (3H, s), 2.51 (3H, s), 2.99 (1H, d, J=5.1 Hz), 3.05 (1H, d, J=5.1 Hz), 7.79 (2H, m), 8.01 (1H, m), 9.98 (1H, s).

Aufarbeitung

  1. filtrationThe precipitated m-chlorobenzoic acid was filtered
  2. extractionthe filtrate was extracted with 1 M Na2CO3 (4×60 ml)
  3. dry with materialThe organic phase was dried over Na2SO4
  4. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-a4fefa8b0ee04372b90ef435b6123c9a
Quelldatensatz
uspto-grants-2008_06
Patentnummer
US07390923B2

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