Nitroformic Acid → 4-Nitrobenzamide

HRID 2352992

Reaktionsgleichung

Reaktionsgleichung von HRID 2352992
[N+:1]([C:4](O)=[O:5])([O-])=O.Cl.CN(C)CCCN=C=NCC.[OH2:19].[OH:20][N:21]1[C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][C:24]=2N=N1>CN(C=O)C.ClCCl>[N+:21]([C:25]1[CH:24]=[CH:29][C:28]([C:4]([NH2:1])=[O:5])=[CH:27][CH:26]=1)([O-:20])=[O:19]

Komponenten

6

Edukt 3

HCID 88689Nitroformic AcidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrate

Produkt 1

HCID 120914-Nitrobenzamide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A mixture of nitrocarboxylic acid (NB-2 or NB-3; 1.2 equivalents), amine (A13, A14 or A16; 1.1 equivalents), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (1.2 equivalents), and 1-hydroxybenzotriazole hydrate (1.2 equivalents) in DMF (0.79 M) was stirred at room temperature for 4 hours. The mixture was diluted with dichloromethane (100 mL) and washed with aqueous saturated sodium bicarbonate solution (50 mL). The aqueous layer was re-extracted with dichloromethane (2×50 mL) and the combined organic solution was dried (Na2SO4), filtered and evaporated under reduced pressure. The crude mixture was purified on silica gel column to provide the 4-nitrobenzamide (NB-2-A13, NB-2-A14 or NB-3-A16).

Aufarbeitung

  1. washwashed with aqueous saturated sodium bicarbonate solution (50 mL)
  2. extractionThe aqueous layer was re-extracted with dichloromethane (2×50 mL)
  3. dry with materialthe combined organic solution was dried (Na2SO4)
  4. filtrationfiltered
  5. customevaporated under reduced pressure
  6. customThe crude mixture was purified on silica gel column

Quellen und Nachweise

ORD-Eintrag
ord-d8a31030a5384adb8d45fd76dc799c9c
Quelldatensatz
uspto-grants-2010_07
Patentnummer
US07749530B2

Verknüpfte Notizen

Wird geladen…