Benzylamine → N-benzyl-5-bromo-2-methoxybenzamide

HRID 518274

Reaktionsgleichung

Reaktionsgleichung von HRID 518274
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([O:11][CH3:12])=[C:6]([CH:10]=1)[C:7]([OH:9])=O.[CH2:13]([NH2:20])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1.N(C(C)C)(C(C)C)CC>CN(C=O)C.C(Cl)Cl>[CH2:13]([NH:20][C:7](=[O:9])[C:6]1[CH:10]=[C:2]([Br:1])[CH:3]=[CH:4][C:5]=1[O:11][CH3:12])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Komponenten

8

Edukt 5

HCID 7504BenzylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 8817395-Bromo-2-methoxybenzoic acid

Produkt 1

HCID 1254086N-benzyl-5-bromo-2-methoxybenzamideAusbeute 90,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To an ice bath cooled mixture of 5-bromo-2-methoxybenzoic acid (439 mg, 1.9 mmol) in 1:1 CH2Cl2:DMF (4 mL) was added benzylamine (0.228 mL, 2.1 mmol), EDCI (438 mg, 2.3 mmol), HOBt (311 mg, 2.3 mmol) and NEtiPr2 (0.496 mL, 2.85 mmol). The mixture was then stirred at room temperature until the reaction was complete. Extractive work up with ethyl acetate, washing with saturated aqueous NaHCO3, H2O, saturated aqueous KHSO4 and brine, gave the title compound (550 mg) after isolation which was carried forward without purification. LCMS (M+H)+ 320, 322.

Aufarbeitung

  1. temperatureTo an ice bath cooled
  2. washExtractive work up with ethyl acetate, washing with saturated aqueous NaHCO3, H2O, saturated aqueous KHSO4 and brine

Quellen und Nachweise

ORD-Eintrag
ord-dd64335374804bb4a10dd1a978b38bf4
Quelldatensatz
uspto-grants-2015_08
Patentnummer
US09115114B2

Verknüpfte Notizen

Wird geladen…