Benzoyl chloride, 3-bromo- → 3-Bromo-N-methoxy-N-methylbenzamide

HRID 30554

Reaktionsgleichung

Reaktionsgleichung von HRID 30554
Cl.[CH3:2][O:3][NH:4][CH3:5].C(N(C(C)C)CC)(C)C.[Br:15][C:16]1[CH:17]=[C:18]([CH:22]=[CH:23][CH:24]=1)[C:19](Cl)=[O:20]>C(Cl)Cl>[Br:15][C:16]1[CH:17]=[C:18]([CH:22]=[CH:23][CH:24]=1)[C:19]([N:4]([O:3][CH3:2])[CH3:5])=[O:20]

Komponenten

5

Edukt 3

HCID 74377Benzoyl chloride, 3-bromo-HCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 81531Diisopropylethylamine

Produkt 1

HCID 121628753-Bromo-N-methoxy-N-methylbenzamideAusbeute 90,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

A mixture of N-methoxymethanamine hydrochloride (22.1 g, 228.5 mmol), diisopropyl ethyl amine (63.5 mL, 365.6 mmol) and CH2Cl2 was treated dropwise with 3-bromobenzoyl chloride (15 g, 68.5 mmol) in CH2Cl2, stirred at room temperature for 30 minutes, and concentrated under vacuum. The resultant residue was dispersed in water and extracted with ethyl ether. The organic extracts were combined, dried over MgSO4 and concentrated in vacuo. The resultant residue was purified on silica gel (Biotage) using hexanes/EtOAc (2/1) as the eluting solvents to give 3-bromo-N-methoxy-N-methylbenzamide as a tan solid (15.1 g, 90% yield).

Aufarbeitung

  1. concentrationconcentrated under vacuum
  2. additionThe resultant residue was dispersed in water
  3. extractionextracted with ethyl ether
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo
  6. customThe resultant residue was purified on silica gel (Biotage)

Quellen und Nachweise

ORD-Eintrag
ord-166da1d9e33a4bd8acda9bd0700ddbfe
Quelldatensatz
uspto-grants-2008_09
Patentnummer
US07423158B2

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