StartseiteMCPWorkbenchSkills
StartseiteWorkbenchBenachrichtigungenMein Bereich
llms.txt · MCP-AnleitungDatenschutz · Nutzungsbedingungen · Supportv1.8.0
  1. Startseite
  2. /Reaktion

Cyclohexylamine → N-cyclohexyl-5-nitro-1H-indazole-3-carboxamide

HRID 25395
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 25395
[N+:1]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][N:8]=[C:7]2[C:13]([OH:15])=O)([O-:3])=[O:2].O[N:17]1[C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=2N=N1.Cl.C(N=C=NCCCN(C)C)C.C1(N)CCCCC1>O.ClCCl.C(N(CC)CC)C.CN(C)C=O>[CH:21]1([NH:17][C:13]([C:7]2[C:6]3[C:10](=[CH:11][CH:12]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=3)[NH:9][N:8]=2)=[O:15])[CH2:22][CH2:23][CH2:24][CH2:25][CH2:20]1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

9

Edukt 4

HCID 7965CyclohexylamineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 71446525-nitro-1H-indazole-3-carboxylic Acid

Produkt 1

HCID 22567295N-cyclohexyl-5-nitro-1H-indazole-3-carboxamideAusbeute 459,9 %

Reagenzien, Katalysatoren, Lösungsmittel

4
HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittelHCID 6344DichloromethaneLösungsmittel2×HCID 8471TriethylamineLösungsmittel

Versuchsvorschrift

N-Cyclohexyl-5-nitro-1H-indazole-3-carboxamide can be obtained in the following way: a solution of 2.5 g of 5-nitro-1H-indazole-3-carboxylic acid, of 150 ml of dichloromethane, of 75 ml of dimethylformamide, 0.16 g of 1-hydroxybenzotriazole and of 2.75 g 1-ethyl-3-[3-(dimethylamino)propyl]carbodiimide hydrochloride is stirred for 15 minutes at a temperature of 25° C. 1.7 ml of cyclohexylamine and 1.7 ml of triethylamine are then added. The reaction medium is maintained with stirring for 70 hours and concentrated by evaporation under reduced pressure. The residue thus obtained is taken up with 50 ml of dichloromethane and 50 ml of diisopropyl ethyl. After filtration, the paste obtained is taken up with 80 ml of distilled water and the solid form is filtered through a sintered glass funnel, washed with two times 50 ml of water and then dried under reduced pressure. The resulting solid is taken up with 50 ml of ethyl acetate, filtered through a sintered glass filter, washed with two times 25 ml of ethyl acetate and dried at 50° C. under reduced pressure. 1.57 g of N-cyclohexyl-5-nitro-1H-indazole-3-carboxamide are thus obtained in the form of a beige solid (Rf=0.90, silica gel thin layer chromatography, eluent: chloroform/methanol/20% aqueous ammonia (12/3/0.5 by volume)).

Aufarbeitung

  1. temperatureThe reaction medium is maintained
  2. concentrationconcentrated by evaporation under reduced pressure
  3. customThe residue thus obtained
  4. filtrationAfter filtration
  5. customthe paste obtained
  6. filtrationthe solid form is filtered through a sintered glass funnel
  7. washwashed with two times 50 ml of water
  8. customdried under reduced pressure
  9. filtrationfiltered through a sintered glass
  10. filtrationfilter
  11. washwashed with two times 25 ml of ethyl acetate
  12. customdried at 50° C. under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-712968c199714d1c9b6993c7f837df5b
Quelldatensatz
uspto-grants-2005_02
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06858638B2

Notizen zur Reaktion

Wird geladen…

Auf dieser SeiteKomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion