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

Phosgene → 1-[5-Tert-butyl-3-methylcarbamoyl-2-methoxyphenyl]-3-[4-(4-pyridinyloxy)-naphthalen-1-yl]-urea

HRID 1884601
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1884601
[NH2:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([O:12][C:13]2[CH:18]=[CH:17][N:16]=[CH:15][CH:14]=2)=[CH:4][CH:3]=1.[C:19](=O)(O)[O-:20].[Na+].C(Cl)(Cl)=O.[C:28]([C:32]1[CH:33]=[C:34]([C:41](=[O:44])[NH:42][CH3:43])[C:35]([O:39][CH3:40])=[C:36]([CH:38]=1)[NH2:37])([CH3:31])([CH3:30])[CH3:29]>ClCCl>[C:28]([C:32]1[CH:33]=[C:34]([C:41](=[O:44])[NH:42][CH3:43])[C:35]([O:39][CH3:40])=[C:36]([NH:37][C:19]([NH:1][C:2]2[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]([O:12][C:13]3[CH:18]=[CH:17][N:16]=[CH:15][CH:14]=3)=[CH:4][CH:3]=2)=[O:20])[CH:38]=1)([CH3:31])([CH3:29])[CH3:30]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 6371PhosgeneHCID 516892Sodium BicarbonateHCID 235058205-Tert-butyl-2-methoxy-3-methylcarbamoylanilineHCID 235058621-Amino-4-(4-pyridinyl)oxynaphthalene

Produkt 1

HCID 235058751-[5-Tert-butyl-3-methylcarbamoyl-2-methoxyphenyl]-3-[4-(4-pyridinyloxy)-naphthalen-1-yl]-urea

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

1-Amino-4-(4-pyridinyloxy)naphthalene (Example 6) (1.0 mmol) is dissolved in dichloromethane (15 mL). An equal volume of sat. aqueous sodium bicarbonate is added, and the biphasic solution is cooled to 0° C. During the addition of phosgene (1.93 M in toluene, 1.0 mL), stirring is stopped. Immediately afterward, stirring is resumed for 15 min with the reaction mixture at 0° C. The layers are separated, the organics dried over solid magnesium sulfate and concentrated to approximately 5 mL of solution. 5-tert-Butyl-3-methylcarbamoyl-2-methoxyaniline (Example 3) (0.9 mmol) in dichloromethane (5 mL) is added, and the reaction mixture is stirred overnight at ambient temperature. The solvent is removed by rotary evaporation and the resulting product purified by flash chromatography over silica gel with a suitable elutant such as CH2Cl2:MeOH (95:5) to give the title compound.

Aufarbeitung

  1. stirringImmediately afterward, stirring
  2. customThe layers are separated
  3. dry with materialthe organics dried over solid magnesium sulfate
  4. concentrationconcentrated to approximately 5 mL of solution
  5. stirringthe reaction mixture is stirred overnight at ambient temperature
  6. customThe solvent is removed by rotary evaporation
  7. customthe resulting product purified by flash chromatography over silica gel with a suitable elutant such as CH2Cl2:MeOH (95:5)

Quellen und Nachweise

ORD-Eintrag
ord-3b5395b801904d60bfce1a1f418e8012
Quelldatensatz
uspto-grants-2004_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06765009B2

Notizen zur Reaktion

Wird geladen…

Auf dieser SeiteKomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion