1-Hydroxybenzotriazole → 2-fluoro-5-nitro-N-(1,3-benzodioxol-5-ylmethyl)benzamide

HRID 1934644

Reaktionsgleichung

Reaktionsgleichung von HRID 1934644
[F:1][C:2]1[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[CH:7][C:3]=1[C:4]([OH:6])=O.[O:14]1[C:18]2[CH:19]=[CH:20][C:21]([CH2:23][NH2:24])=[CH:22][C:17]=2[O:16][CH2:15]1.Cl.CN(C)CCCN=C=NCC.ON1C2C=CC=CC=2N=N1>CN(C)C=O>[F:1][C:2]1[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[CH:7][C:3]=1[C:4]([NH:24][CH2:23][C:21]1[CH:20]=[CH:19][C:18]2[O:14][CH2:15][O:16][C:17]=2[CH:22]=1)=[O:6]

Komponenten

6

Edukt 4

HCID 757711-HydroxybenzotriazoleHCID 75799Benzo-1,3-dioxole-5-methylamineHCID 2809972-Fluoro-5-nitrobenzoic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Produkt 1

HCID 224676412-fluoro-5-nitro-N-(1,3-benzodioxol-5-ylmethyl)benzamideAusbeute 86,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A mixture of 2-fluoro-5-nitrobenzoic acid (1.00 g), (1,3-benzodioxol-5-ylmethyl)amine (980 mg), 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride (1.55 g) and 1-hydroxybenzotriazole (1.09 g) in anhydrous dimethylformamide (10 mL) was stirred for 40 hours at ambient temperature. The mixture was partitioned between water and ethyl acetate. The separated organic layer was washed with an aqueous saturated sodium bicarbonate solution, 1N-hydrochloric acid, water and brine. Then, the resultant was dried over magnesium sulfate and evaporated in vacuo. The residue was triturated with diisopropyl ether to give 2-fluoro-5-nitro-N-(1,3-benzodioxol-5-ylmethyl)benzamide as yellow powders (1.48 g).

Aufarbeitung

  1. customThe mixture was partitioned between water and ethyl acetate
  2. washThe separated organic layer was washed with an aqueous saturated sodium bicarbonate solution, 1N-hydrochloric acid, water and brine
  3. dry with materialThen, the resultant was dried over magnesium sulfate
  4. customevaporated in vacuo
  5. customThe residue was triturated with diisopropyl ether

Quellen und Nachweise

ORD-Eintrag
ord-829a96a6ccff41a995f08c54de850f1f
Quelldatensatz
uspto-grants-2002_05
Patentnummer
US06384080B1

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