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

Tetrahydrofuran → Ethyl 2-[7-amino-1-(methoxymethyl)-1H-indol-2-yl]-1,3-thiazole-5-carboxylate

HRID 1851375
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1851375
[CH3:1][O:2][CH2:3][N:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][C:11]=2[N+:13]([O-])=O)[CH:6]=[C:5]1[C:16]1[S:17][C:18]([C:21]([O:23][CH2:24][CH3:25])=[O:22])=[CH:19][N:20]=1.O1CCCC1.O.NN>O.O.O.O.O.O.[Fe](Cl)(Cl)Cl.C(O)C>[NH2:13][C:11]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:12]=1[N:4]([CH2:3][O:2][CH3:1])[C:5]([C:16]1[S:17][C:18]([C:21]([O:23][CH2:24][CH3:25])=[O:22])=[CH:19][N:20]=1)=[CH:6]2
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 3

HCID 8028TetrahydrofuranHCID 24654Hydrazine hydrate (1:1)HCID 57901708ethyl 2-[1-(methoxymethyl)-7-nitro-1H-indol-2-yl]-1,3-thiazole-5-carboxylate

Produkt 1

HCID 57901657Ethyl 2-[7-amino-1-(methoxymethyl)-1H-indol-2-yl]-1,3-thiazole-5-carboxylateAusbeute 97,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 16211236
Trichloroiron;hexahydrate
Katalysator
HCID 702EthanolLösungsmittel

Versuchsvorschrift

A mixture of ethyl 2-[1-(methoxymethyl)-7-nitro-1H-indol-2-yl]-1,3-thiazole-5-carboxylate (2.44 g), iron(III) chloride hexahydrate (92 mg), activated carbon (1.0 g), tetrahydrofuran (10 mL) and ethanol (5 mL) was heated under reflux for 20 min. To the reaction mixture was added hydrazine monohydrate (2.05 g) over 15 min while heating under reflux. The reaction mixture was heated under reflux for 5 hr, filtrated, and the filtrate was concentrated. The residue was dissolved in ethyl acetate, washed with saturated brine, dried (MgSO4), and concentrated. Isopropyl ether was added to the obtained residue. The resulting crystals were collected by filtration, washed with isopropyl ether, and dried to give the title compound (2.18 g, yield 97%) as yellow crystals. melting point 188-190° C.

Aufarbeitung

  1. temperaturewas heated
  2. temperatureunder reflux for 20 min
  3. temperaturewhile heating
  4. temperatureunder reflux
  5. temperatureThe reaction mixture was heated
  6. temperatureunder reflux for 5 hr
  7. filtrationfiltrated
  8. concentrationthe filtrate was concentrated
  9. dissolutionThe residue was dissolved in ethyl acetate
  10. washwashed with saturated brine
  11. dry with materialdried (MgSO4)
  12. concentrationconcentrated
  13. additionIsopropyl ether was added to the obtained residue
  14. filtrationThe resulting crystals were collected by filtration
  15. washwashed with isopropyl ether
  16. customdried

Quellen und Nachweise

ORD-Eintrag
ord-aef80e8d3dbb4cb8a704688f7842e39f
Quelldatensatz
uspto-grants-2015_02
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08957070B2

Notizen zur Reaktion

Wird geladen…

Auf dieser SeiteKomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion