Hydrochloric Acid → 2-Benzylthiazolo[4,5-c]quinolin-4-amine hydrochloride

HRID 430548Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 430548
[CH2:1]([C:8]1[S:9][C:10]2[C:19]3[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=3[N:13]=[C:12]([NH:20]C(=O)C(Cl)(Cl)[Cl:23])[C:11]=2[N:27]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C[O-].[Na+].Cl>CO.C(O)(C)C>[ClH:23].[CH2:1]([C:8]1[S:9][C:10]2[C:19]3[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=3[N:13]=[C:12]([NH2:20])[C:11]=2[N:27]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Komponenten

6

Edukt 3

HCID 313Hydrochloric AcidHCID 10942334Sodium MethoxideHCID 22648314HCID 22648314, Verbindung

Produkt 1

HCID 226482692-Benzylthiazolo[4,5-c]quinolin-4-amine hydrochloride

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittel2×HCID 3776IsopropanolLösungsmittel

Versuchsvorschrift

Trichloroacetyl isocyanate (1.2 mL, 10.3 mmol) was added to a solution of 2-benzylthiazolo[4,5-c]quinoline-5N-oxide (2.0 g, 6.8 mmol) in dichloromethane (100 mL). The reaction mixture was stirred at ambient temperature for 2 hours and then concentrated to provide crude N-(2-benzylthiazolo[4,5-c]quinolin-4-yl)trichloroacetamide. The amide was dissolved in methanol. Sodium methoxide (1 equivalent) was added. The reaction mixture was heated on a steam bath for 30 minutes and then allowed to cool to ambient temperature. The resulting precipitate was isolated by filtration and then suspended in a mixture of methanol and isopropanol. Hydrochloric acid (1 equivalent) was added and all of the solid dissolved initially. A white solid crystallized out. This material was isolated by filtration, washed with isopropanol and then dried to provide 1.5 g of 2-benzylthiazolo[4,5-c]quinolin-4-amine hydrochloride, m.p. 152-155° C. Analysis: Calculated for: C17H13N3S HCl: % C, 62.28; % H, 4.30; % N, 12.82; Found: % C, 62.05; % H, 4.23; % N, 12.82.

Aufarbeitung

  1. temperatureThe reaction mixture was heated on a steam bath for 30 minutes
  2. customThe resulting precipitate was isolated by filtration
  3. dissolutionall of the solid dissolved initially
  4. customA white solid crystallized out
  5. customThis material was isolated by filtration
  6. washwashed with isopropanol
  7. customdried

Quellen und Nachweise

ORD-Eintrag
ord-8fa99fbe141a4d93a0b4da66a8233692
Quelldatensatz
uspto-grants-2001_11
Patentnummer
US06323200B1

Notizen zur Reaktion

Wird geladen…