Hydrochloric Acid → 6,7-Dimethoxy-4-(2-oxo-2,3-dihydro-benzothiazol-6-ylamino)-quinoline-3-carbonitrile

HRID 1595781Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1595781
Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:14][CH3:15])=[C:9]([O:12][CH3:13])[CH:10]=2)[N:5]=[CH:4][C:3]=1[C:16]#[N:17].[NH2:18][C:19]1[CH:28]=[CH:27][C:22]2[NH:23][C:24](=[O:26])[S:25][C:21]=2[CH:20]=1.Cl.N1C=CC=CC=1.C(OC(O)C)C.C(=O)([O-])[O-].[Na+].[Na+].Cl>O>[CH3:13][O:12][C:9]1[CH:10]=[C:11]2[C:6](=[CH:7][C:8]=1[O:14][CH3:15])[N:5]=[CH:4][C:3]([C:16]#[N:17])=[C:2]2[NH:18][C:19]1[CH:28]=[CH:27][C:22]2[NH:23][C:24](=[O:26])[S:25][C:21]=2[CH:20]=1

Komponenten

8

Edukt 6

HCID 313Hydrochloric AcidHCID 10340Sodium CarbonateHCID 64533292(3H)-Benzothiazolone, 6-amino-HCID 101298981-EthoxyethanolHCID 10176127Pyridinium chlorideHCID 105866764-Chloro-6,7-dimethoxy-quinoline-3-carbonitrile

Produkt 1

HCID 101342476,7-Dimethoxy-4-(2-oxo-2,3-dihydro-benzothiazol-6-ylamino)-quinoline-3-carbonitrileAusbeute 86,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

A mixture of 0.249 g of 4-chloro-6,7-dimethoxy-quinolin-3-carbonitrile, 0.166 g of 6-amino-2-benzothiazolinone, 0.020 g of pyridine hydrochloride, and 10 ml of ethoxyethanol was stirred under nitrogen, at reflux temperature for 20 minutes. The mixture was cooled and added to 40 ml of water. To this mixture was added sodium carbonate and concentrated hydrochloric acid to adjust pH to 7. The product was collected, washed with water, and dried to give 0.326 g of 6,7-dimethoxy-4-(2-oxo-2,3-dihydro-benzothiazol-6-ylamino)-quinoline-3-carbonitrile as a solid, mp 285-287° C.; mass spectrum (electrospray, m/e): M+H 379.0858.

Aufarbeitung

  1. temperatureat reflux temperature for 20 minutes
  2. temperatureThe mixture was cooled
  3. customThe product was collected
  4. washwashed with water
  5. customdried

Quellen und Nachweise

ORD-Eintrag
ord-ac6de107a99140b59bbe9602d974e36c
Quelldatensatz
uspto-grants-2001_09
Patentnummer
US06288082B1

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