Sodium hydride → 1-(4-Amino-6-(methylthio)-1,3,5-triazin-2-yl)ethanol

HRID 1845867Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1845867
Cl.[OH:2][CH:3]([CH3:7])[C:4](=[NH:6])[NH2:5].[H-].[Na+].[C:10]([N:12]=[C:13](SC)[S:14][CH3:15])#[N:11]>CN(C)C=O>[NH2:11][C:10]1[N:12]=[C:13]([S:14][CH3:15])[N:5]=[C:4]([CH:3]([OH:2])[CH3:7])[N:6]=1

Komponenten

5

Edukt 3

HCID 24758Sodium hydrideHCID 66289Dimethyl N-cyanodithioiminocarbonateHCID 223286992-Hydroxypropanimidamide hydrochloride

Produkt 1

HCID 672579331-(4-Amino-6-(methylthio)-1,3,5-triazin-2-yl)ethanolAusbeute 4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
65 °C

Versuchsvorschrift

Under a nitrogen atmosphere 2-hydroxypropanimidamide hydrochloride (4.97 g) was suspended in dry N,N-dimethylformamide (25 mL) and sodium hydride (1.66 g, 60 wt % in mineral oil) was added in one portion. When gas evolution ceased the white suspension was heated to 65° C. After 1 h dimethyl cyanocarbonimidodithioate (6.24 g) was added and the mixture was stirred at 65° C. for 18 hours. The reaction mixture was concentrated and triturated with water (200 mL). The resulting precipitate was filtered off, washed with water and the aqueous layer was extracted with 5% methanol in dichloromethane (3×100 mL). The combined organic extracts were dried (sodium sulfate) and concentrated before being purified by flash chromatography eluting with 10% methanol in dichloromethane to give the title compound (300 mg) as a yellow oil that solidified on standing.

Aufarbeitung

  1. concentrationThe reaction mixture was concentrated
  2. customtriturated with water (200 mL)
  3. filtrationThe resulting precipitate was filtered off
  4. washwashed with water
  5. extractionthe aqueous layer was extracted with 5% methanol in dichloromethane (3×100 mL)
  6. dry with materialThe combined organic extracts were dried (sodium sulfate)
  7. concentrationconcentrated
  8. custombefore being purified by flash chromatography
  9. washeluting with 10% methanol in dichloromethane

Quellen und Nachweise

ORD-Eintrag
ord-2bbc8ec5401b4bc1b1c6e6b37d32914b
Quelldatensatz
uspto-grants-2015_02
Patentnummer
US08952001B2

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