Guanidine Hydrochloride → HCID 10200445, Verbindung

HRID 2415111Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2415111
[Br:1][C:2]1[C:11]2[C:6](=[C:7]([O:24][CH3:25])[CH:8]=[C:9]([CH2:12][C:13](=[CH:16]NC3C=CC=CC=3)[C:14]#[N:15])[CH:10]=2)[O:5][C:4]([CH3:27])([CH3:26])[CH:3]=1.Cl.[NH2:29][C:30]([NH2:32])=[NH:31].CC(C)([O-])C.[K+]>C(O)C>[Br:1][C:2]1[C:11]2[C:6](=[C:7]([O:24][CH3:25])[CH:8]=[C:9]([CH2:12][C:13]3[C:14]([NH2:15])=[N:31][C:30]([NH2:32])=[N:29][CH:16]=3)[CH:10]=2)[O:5][C:4]([CH3:27])([CH3:26])[CH:3]=1

Komponenten

5

Edukt 3

HCID 5742Guanidine HydrochlorideHCID 23665647Potassium tert-butoxideHCID 69898773HCID 69898773, Verbindung

Produkt 1

HCID 10200445HCID 10200445, VerbindungAusbeute 48,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

The above prepared 418 mg of 2-(4-bromo-8-methoxy-2,2-dimethyl-2H-chromen-6-ylmethyl)-3-phenylamino-acrylonitrile were treated with 248 mg of guanidine hydrochloride (3.3 eq.), 291 mg of potassium-t-butoxide (3.3 eq.) and 16 ml of ethanol and heated under reflux under argon atmosphere for 14 hours. After cooling, the reaction mixture was poured onto crushed ice, extracted twice with AcOEt, washed with water and brine, dried over magnesium sulfate and evaporated to dryness. Flash chromatography (SiO2 with CH2Cl2/MeOH/25% NH3=19/1/0.05), followed by crystallization from EtOEt afforded 186 mg of the title compound as light-yellow crystals, mp.238-239°.

Aufarbeitung

  1. temperatureheated
  2. temperatureunder reflux under argon atmosphere for 14 hours
  3. temperatureAfter cooling
  4. additionthe reaction mixture was poured
  5. customonto crushed ice
  6. extractionextracted twice with AcOEt
  7. washwashed with water and brine
  8. dry with materialdried over magnesium sulfate
  9. customevaporated to dryness
  10. customFlash chromatography (SiO2 with CH2Cl2/MeOH/25% NH3=19/1/0.05), followed by crystallization from EtOEt

Quellen und Nachweise

ORD-Eintrag
ord-c54654863e464979ba5e29ba4c012c42
Quelldatensatz
uspto-grants-2004_11
Patentnummer
US06818649B2

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