Phenyl Isothiocyanate → HCID 178490875, Verbindung

HRID 72690

Reaktionsgleichung

Reaktionsgleichung von HRID 72690
[C:1]1([N:7]=[C:8]=S)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[NH:10]([C:12]1[N:17]([CH2:18][C:19]2[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=2)[C:16](=[O:27])[N:15]([CH3:28])[C:14](=[O:29])[CH:13]=1)[NH2:11]>CN(C=O)C>[CH3:26][O:25][C:22]1[CH:21]=[CH:20][C:19]([CH2:18][N:17]2[C:12]3[NH:10][N:11]=[C:8]([NH:7][C:1]4[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=4)[C:13]=3[C:14](=[O:29])[N:15]([CH3:28])[C:16]2=[O:27])=[CH:24][CH:23]=1

Komponenten

4

Edukt 2

HCID 7673Phenyl IsothiocyanateHCID 667954896-hydrazinyl-1-(4-methoxybenzyl)-3-methylpyrimidine-2,4(1H,3H)-dione

Produkt 1

HCID 178490875HCID 178490875, VerbindungAusbeute 414 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

Phenyl isothiocyanate (3.9 mL, 32.7 mmol) is added to a suspension of 6-hydrazinyl-1-(4-methoxybenzyl)-3-methylpyrimidine-2,4(1H,3H)-dione (0.45 g, 1.6 mmol) in DMF (12 mL). The reaction mixture is heated at 120° C. for 40 hours, and then evaporated to remove solvent under reduced pressure. The residue is washed with hexanes, and then treated with MeOH (125 mL), and stored at −15° C. for 2 days to give a crystalline solid. The solid is recrystallized from CH3OH-EtOAc to afford 2.5 g of product (Yield: 61%). 1H NMR (400 MHz, DMSO-d6) δ3.21 (s, 3H), 3.73 (s, 3H), 5.01 (s, 2H), 6.88-7.36 (m, 9H). MS (FAB) m/z 378.3 [M+H]+.

Aufarbeitung

  1. customevaporated
  2. customto remove solvent under reduced pressure
  3. washThe residue is washed with hexanes
  4. additiontreated with MeOH (125 mL)
  5. customto give a crystalline solid
  6. customThe solid is recrystallized from CH3OH-EtOAc

Quellen und Nachweise

ORD-Eintrag
ord-86cd04daa4e24f2dad931c11784256e7
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08829008B2

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