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

Cyanamide → [4-Amino-2-[4-(2-dimethylaminoethoxy)-phenylamino]-thiazol-5-yl]-(3-methoxy-phenyl)-methanone

HRID 2415293
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2415293
[N:1]([C:4]1[CH:15]=[CH:14][C:7]([O:8][CH2:9][CH2:10][N:11]([CH3:13])[CH3:12])=[CH:6][CH:5]=1)=[C:2]=[S:3].[N:16]#[C:17][NH2:18].CC(C)([O-])C.[K+].Br[CH2:26][C:27]([C:29]1[CH:34]=[CH:33][CH:32]=[C:31]([O:35][CH3:36])[CH:30]=1)=[O:28]>C(#N)C.C(O)(C)(C)C.CCOCC.Cl.CCOCC>[NH2:16][C:17]1[N:18]=[C:2]([NH:1][C:4]2[CH:15]=[CH:14][C:7]([O:8][CH2:9][CH2:10][N:11]([CH3:12])[CH3:13])=[CH:6][CH:5]=2)[S:3][C:26]=1[C:27]([C:29]1[CH:34]=[CH:33][CH:32]=[C:31]([O:35][CH3:36])[CH:30]=1)=[O:28]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

9

Edukt 4

HCID 9864CyanamideHCID 101294Bromomethyl 3-methoxyphenyl ketoneHCID 226409714-[2-(Dimethylamino)ethoxy]phenyl isothiocyanateHCID 23665647Potassium tert-butoxide

Produkt 1

HCID 10001723[4-Amino-2-[4-(2-dimethylaminoethoxy)-phenylamino]-thiazol-5-yl]-(3-methoxy-phenyl)-methanoneAusbeute 42 %

Reagenzien, Katalysatoren, Lösungsmittel

4
HCID 3283Diethyl EtherLösungsmittelHCID 6342AcetonitrileLösungsmittelHCID 6386tert-ButanolLösungsmittelHCID 10953452Ether hydrochlorideLösungsmittel

Versuchsvorschrift

To a stirred mixture of [2-(4-isothiocyanato-phenoxy)-ethyl]-dimethylamine (0.6 g, 2.7 mmol) (from Step A) and cyanamide (0.123 g, 2.95 mmol) in acetonitrile (10 mL) and tert-butanol (10 mL), a solution of potassium tert-butoxide (2.7 mL, 1.0 M in tert-BuOH) was added. After 30 minutes at room temperature, 2-bromo-3′-methoxyacetophenone was added. The reaction mixture was stirred at room temperature for 1 hour and then refluxed for 1 hour. The chilled reaction mixture was diluted with ether and excess anhydrous hydrochloric acid/ether solution was added. The solids were filtered, washed with ether and then dissolved in dichloromethane/aqueous sodium bicarbonate. The dried (Na2SO4) organic solution was diluted with toluene (25 mL), concentrated, and refluxed to remove dichloromethane, The cooled mixture was diluted with hexane and filtered to give 0.47 g (42%) of [4-amino-2-[4-(2-dimethylaminoethoxy)-phenylamino]-thiazol-5-yl]-(3-methoxy-phenyl)-methanone as a yellow solid, mp 130° C. (dec). Mass spectrum (ES) MH+=413.

Aufarbeitung

  1. temperaturerefluxed for 1 hour
  2. customThe chilled reaction mixture
  3. additionwas added
  4. filtrationThe solids were filtered
  5. washwashed with ether
  6. dissolutiondissolved in dichloromethane/aqueous sodium bicarbonate
  7. dry with materialThe dried (Na2SO4) organic solution
  8. additionwas diluted with toluene (25 mL)
  9. concentrationconcentrated
  10. temperaturerefluxed
  11. customto remove dichloromethane
  12. additionThe cooled mixture was diluted with hexane
  13. filtrationfiltered

Quellen und Nachweise

ORD-Eintrag
ord-aa9db080915744bb9a8fdb830efbbac9
Quelldatensatz
uspto-grants-2004_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06818663B2

Notizen zur Reaktion

Wird geladen…

Auf dieser SeiteKomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion