Sodium hydride → 2-Thiocyanomethyl-3-allyl-4(3H)-quinazolinone

HRID 364624

Reaktionsgleichung

Reaktionsgleichung von HRID 364624
S[C:2]1[N:11]([CH2:12][CH:13]=[CH2:14])[C:10](=[O:15])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.Cl[CH2:17][S:18][C:19]#[N:20].[H-].[Na+]>C(COC)OC>[S:18]([CH2:17][C:2]1[N:11]([CH2:12][CH:13]=[CH2:14])[C:10](=[O:15])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1)[C:19]#[N:20]

Komponenten

5

Edukt 3

HCID 24758Sodium hydrideHCID 76755Thiocyanic acid, chloromethyl esterHCID 178456612HCID 178456612, Verbindung2×

Produkt 1

HCID 202395102-Thiocyanomethyl-3-allyl-4(3H)-quinazolinone

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 80711,2-DimethoxyethaneLösungsmittel

Versuchsvorschrift

To a mixture of 5.8 g (0.03 mole) 2-mercapto-3-allyl-4(3H)-quinazolinone (the product of Example 5) in 200 ml dimethoxyethane, 5.4 g (0.05 mole) chloromethyl thiocyanate and 2.4 g (0.05 mole) 50% sodium hydride were added. The resulting mixture was stirred overnight at ambient temperature, refluxed at 50° C. for 8 hours, stirred overnight, refluxed at 50° C. for 8 hours and stirred overnight. The reaction mixture was washed with water, extracted with methylene chloride, dried over magnesium sulfate and stripped. The oily residue was triturated with ether, to give the above-identified product, as a solid, melting point 73°-76° C.

Aufarbeitung

  1. temperaturerefluxed at 50° C. for 8 hours
  2. stirringstirred overnight
  3. temperaturerefluxed at 50° C. for 8 hours
  4. stirringstirred overnight
  5. washThe reaction mixture was washed with water
  6. extractionextracted with methylene chloride
  7. dry with materialdried over magnesium sulfate
  8. customThe oily residue was triturated with ether
  9. customto give the above-identified product

Quellen und Nachweise

ORD-Eintrag
ord-1d22afbe27e840f2a92de4ae2e8d78ce
Quelldatensatz
uspto-grants-1986_08
Patentnummer
US04605657

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