1,1'-Carbonyldiimidazole → 2-Chloro-3-fluoro-N-(tricyclo[3.3.1.13,7]dec-1-ylmethyl)-benzamide

HRID 1532309Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1532309
[Cl:1][C:2]1[C:10]([F:11])=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=O.C(N1C=CN=C1)(N1C=CN=C1)=O.[C:24]12([CH2:34][NH2:35])[CH2:33][CH:28]3[CH2:29][CH:30]([CH2:32][CH:26]([CH2:27]3)[CH2:25]1)[CH2:31]2>CN(C)C=O>[Cl:1][C:2]1[C:10]([F:11])=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([NH:35][CH2:34][C:24]12[CH2:33][CH:28]3[CH2:27][CH:26]([CH2:32][CH:30]([CH2:29]3)[CH2:31]1)[CH2:25]2)=[O:6]

Komponenten

5

Edukt 3

HCID 682631,1'-CarbonyldiimidazoleHCID 86625Tricyclo(3.3.1.13,7)dec-1-ylmethylamineHCID 3026202-Chloro-3-fluorobenzoic acid

Produkt 1

HCID 206700332-Chloro-3-fluoro-N-(tricyclo[3.3.1.13,7]dec-1-ylmethyl)-benzamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A solution of 2-chloro-3-fluorobenzoic acid (0.098 g) and carbonyldiimidazole (0.091 g), in N,N-dimethylformamide (3.0 ml) was stirred for 2.5 hours at room temperature. 1-Adamantanemethylamine (0.1 ml) was then added and stirring continued overnight. The reaction mixture was partitioned between ethyl acetate and 2N hydrochloric acid and the organic layer was separated, washed with 10% aqueous sodium hydroxide, water and brine and then dried over sodium sulphate (Na2SO4). The organic layer was subsequently concentrated under reduced pressure to yield the title compound as a white solid (0.138 g).

Aufarbeitung

  1. customThe reaction mixture was partitioned between ethyl acetate and 2N hydrochloric acid
  2. customthe organic layer was separated
  3. washwashed with 10% aqueous sodium hydroxide, water and brine
  4. dry with materialdried over sodium sulphate (Na2SO4)
  5. concentrationThe organic layer was subsequently concentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-6c75761268064efebe7add7541786ba6
Quelldatensatz
uspto-grants-2001_03
Patentnummer
US06201024B1

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