Benzylethanolamine → N-benzyl-6-bromo-2-fluoro-N-(2-hydroxyethyl)benzamide

HRID 886888Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 886888
[Br:1][C:2]1[C:7]([C:8]([OH:10])=O)=[C:6]([F:11])[CH:5]=[CH:4][CH:3]=1.CN(C)C=O.[CH2:17]([NH:24][CH2:25][CH2:26][OH:27])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.C(N(CC)CC)C>S(Cl)(Cl)=O.O1CCCC1.O>[CH2:17]([N:24]([CH2:25][CH2:26][OH:27])[C:8](=[O:10])[C:7]1[C:2]([Br:1])=[CH:3][CH:4]=[CH:5][C:6]=1[F:11])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Komponenten

8

Edukt 4

HCID 4348BenzylethanolamineHCID 6228DimethylformamideHCID 8471TriethylamineHCID 3026212-Bromo-6-fluorobenzoic acid

Produkt 1

HCID 68578409N-benzyl-6-bromo-2-fluoro-N-(2-hydroxyethyl)benzamideAusbeute 97,5 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittelHCID 24386Thionyl ChlorideLösungsmittel

Versuchsvorschrift

A solution of 6-bromo-2-fluorobenzoic acid (10.0 g, 45.7 mmol) and N,N-dimethylformamide (0.100 ml) in thionylchloride (40 ml) was stirred at 85° C. for 12 hr, and the solvent was evaporated under reduced pressure. The residue was added to a solution of N-benzylethanolamine (6.91 g, 45.7 mmol) and triethylamine (9.55 ml, 68.6 mmol) in tetrahydrofuran (100 ml) under ice-cooling, and the mixture was stirred for 1 hr under ice-cooling and at room temperature for 1 hr. The reaction mixture was poured into water, and the mixture was extracted with ethyl acetate. The extract was washed with water and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure to give the desired product (15.7 g, 97.5%) as an oil.

Aufarbeitung

  1. customthe solvent was evaporated under reduced pressure
  2. temperaturecooling
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe extract was washed with water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customThe solvent was evaporated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-b82cc26e824f49f7b8f03f60f8669ead
Quelldatensatz
uspto-grants-2012_08
Patentnummer
US08247403B2

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