1,2-Dichloroethane → N-methyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzamide

HRID 900170Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 900170
[CH3:1][C:2]1([CH3:18])[C:6]([CH3:8])([CH3:7])[O:5][B:4]([C:9]2[CH:17]=[CH:16][C:12](C(O)=O)=[CH:11][CH:10]=2)[O:3]1.C(Cl)CCl.[CH3:23][NH:24][CH3:25].C1C[O:29]CC1>CN(C1C=CN=CC=1)C.CN(C=O)C.C(OCC)(=O)C>[CH3:23][NH:24][C:25](=[O:29])[C:17]1[CH:16]=[CH:12][CH:11]=[CH:10][C:9]=1[B:4]1[O:5][C:6]([CH3:7])([CH3:8])[C:2]([CH3:1])([CH3:18])[O:3]1

Komponenten

8

Edukt 4

HCID 111,2-DichloroethaneHCID 674DimethylamineHCID 8028TetrahydrofuranHCID 27346214-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)benzoic acid

Produkt 1

HCID 69218561N-methyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzamide

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A mixture of 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoic acid (1.0 g, 4.03 mmol), EDC (0.81 g, 4.23 mmol), and DMAP (catalytic amount) in 3 mL of DMF was stirred at room temperature for 1 hr, and then 2 mL of a 2M solution of N,N-dimethylamine in THF (4 mmol) was added into the reaction mixture. The resulting mixture was stirred at room temperature for 16 h. Ethyl acetate (100 mL) was added and the mixture was washed with saturated sodium bicarbonate and brine. The organic layer was dried over Na2SO4, filtered and the filtrate was concentrated. The solvent was removed to give the title compound which was used without further purification for the next step. Mass Spectrum (ESI) m/e=262 (M+1).

Aufarbeitung

  1. stirringThe resulting mixture was stirred at room temperature for 16 h
  2. washthe mixture was washed with saturated sodium bicarbonate and brine
  3. dry with materialThe organic layer was dried over Na2SO4
  4. filtrationfiltered
  5. concentrationthe filtrate was concentrated
  6. customThe solvent was removed

Quellen und Nachweise

ORD-Eintrag
ord-7c638b9d186d453686c94ce59c87c438
Quelldatensatz
uspto-grants-2008_04
Patentnummer
US07358250B2

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