Benzylamine → N-benzyl-4-bromo-2-methoxybenzamide

HRID 432261Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 432261
[CH2:1]([NH2:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Br:9][C:10]1[CH:15]=[CH:14][C:13]([C:16](Cl)=[O:17])=[C:12]([O:19][CH3:20])[CH:11]=1.C(N(CC)CC)C>ClCCl>[CH2:1]([NH:8][C:16](=[O:17])[C:13]1[CH:14]=[CH:15][C:10]([Br:9])=[CH:11][C:12]=1[O:19][CH3:20])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

5

Edukt 3

HCID 7504BenzylamineHCID 8471TriethylamineHCID 223467824-Bromo-2-methoxybenzoyl chloride

Produkt 1

HCID 22346886N-benzyl-4-bromo-2-methoxybenzamideAusbeute 86 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

Benzylamine (0.69 mL, 6.31 mmol) was added slowly to a mixture of 4-Bromo-2-methoxy-1-benzenecarbonyl chloride (1.5 g, 6.01 mmol) and triethylamine (1.3 mL, 9.02 mmol) in dichloromethane (60 mL). After 3 hours, solvent was removed under reduced pressure. Ethyl acetate was added and the mixture was filtered. The filtrate was concentrated under reduced pressure and the residue was re-crystallized from ethyl acetate/heptane to give N1-benzyl-4-bromo-2-methoxybenzamide (1.654 g, 86%). 1H NMR (DMSO-d6) δ 3.92 (s, 3H), 4.67 (d, J=5.67 Hz, 32H), 7.31 (m, 7H), 8.03 (bs, 1H), 8.13 (d, J=8.41, 1H).

Aufarbeitung

  1. customsolvent was removed under reduced pressure
  2. additionEthyl acetate was added
  3. filtrationthe mixture was filtered
  4. concentrationThe filtrate was concentrated under reduced pressure
  5. customthe residue was re-crystallized from ethyl acetate/heptane

Quellen und Nachweise

ORD-Eintrag
ord-95e98ee7b1dc487b9121ab150653b6ad
Quelldatensatz
uspto-grants-2003_12
Patentnummer
US06660744B1

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