Water → HCID 10774329, Verbindung

HRID 389079Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 389079
Cl[C:2]1[C:3]2[N:4]([CH:12]=[CH:13][N:14]=2)[C:5]2[C:10]([N:11]=1)=[CH:9][CH:8]=[CH:7][CH:6]=2.[CH3:15][NH2:16].O.C(Cl)Cl.CO>CCO.ClCCl>[CH3:15][NH:16][C:2]1[C:3]2[N:4]([CH:12]=[CH:13][N:14]=2)[C:5]2[C:10]([N:11]=1)=[CH:9][CH:8]=[CH:7][CH:6]=2

Komponenten

7

Edukt 4

HCID 962WaterHCID 6329Methylamine2×HCID 107745254-Chloroimidazo[1,2-a]quinoxalineHCID 21226129Dichloromethane methanol

Produkt 1

HCID 10774329HCID 10774329, VerbindungAusbeute 93 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

Compound 12 (0.110 g, 0.54 mmol) is solubilized in EtOH (10 ml), and then a solution of methylamine in water (40% by weight) (0.15 ml, 1.74 mmol) is introduced. The mixture is left under stirring in an autoclave, at room temperature, for at least 15 h. The product, initially insoluble, is solubilized shortly thereafter. The progression of the reaction is controlled by TLC, eluent: CH2Cl2/MeOH (95/5). At the end of 15 h, 1.5 eq (0.06 ml) of methylamine are added. After 5 h of stirring, the reaction progresses no further. The solvent is evaporated dry under vacuum. The yellowish residue obtained is solubilized in dichloromethane (10 ml). This organic phase is washed using a saturated sodium bicarbonate solution (10 ml) and then water (10 ml). It is then dried on Na2SO4 and then evaporated under vacuum. A white solid is recovered. The residue is purified on a silica gel column in order to eliminate traces of the starting product, eluent: CH2Cl2/AcEt (70/30). A white solid (0.99 g, 93%) is obtained; 1H NMR (300 MHz, DMSO-d6) δ: 7.92 (s, 1H, C—CH—N), 7.75 (dd, J1=1.22 Hz, J2=8.17 Hz, 1H, ArH), 7.65 (dd, J1=1.26 Hz, J2=8.06 Hz, 1H, ArH), 7.52 (s, 1H, N—CH—C), 7.4 (t, 1H, ArH), 7.25 (t, 1H, ArH), 6.15 (s, 1H, NH), 3.25 (d, 3H, —CH3); 13C NMR (200 MHz, DMSO-d6) δ: 142.25, 139.17, 131.99, 129.40, 128.17, 127.20, 125.14, 124.34, 114.14, 113.89, 29.20. Analysis calculated for C11H10N4: C, 66.65; H, 5.08; N, 28.26. Experimental: C, 66.26; H, 5.53; N, 28.23.

Aufarbeitung

  1. waitThe mixture is left
  2. stirringAfter 5 h of stirring
  3. customThe solvent is evaporated
  4. customdry under vacuum
  5. customThe yellowish residue obtained
  6. washThis organic phase is washed
  7. customIt is then dried on Na2SO4
  8. customevaporated under vacuum
  9. customA white solid is recovered
  10. customThe residue is purified on a silica gel column in order

Quellen und Nachweise

ORD-Eintrag
ord-5ef19d6a98714b38891d1229685a333e
Quelldatensatz
uspto-grants-2013_02
Patentnummer
US08378098B2

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