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6,7-dimethoxy-4-(2-oxo-2,3-dihydro-benzothiazol-6-ylamino)-quinoline-3-carbonitrile[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
With pyridine hydrochloride; In 1-ethoxyethanol; for 0.333333h;Heating / reflux; Alkaline conditions;
A mixture of 0.249 g of 4-chloro-6,7-dimethoxy-quinolin-3-carbonitrile, 0.166 g of <strong>[56354-98-4]6-amino-2-benzothiazolinone</strong>, 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 285-287C; mass spectrum (electrospray, m/e): M+H 379.0858.
Step B 6-Amino-1,3-benzothiazol-2(3H)-one The compound obtained in Step A (0.036 mol) is dissolved in 90 ml of methanol, and then 2.5 g of palladium-on-carbon and 18 g of ammonium formate are added in succession and the mixture is heated at reflux for 18 hours. 40 ml of dioxane are added and refluxing is continued for 24 hours. The palladium-on-carbon is then filtered off. The reaction mixture is concentrated, the resulting precipitate is filtered off, and the filtrate is evaporated under reduced pressure. The resulting residue is taken up in a 1N hydrochloric acid solution and extracted twice with 50 ml of ethyl acetate each time. The aqueous phase is rendered alkaline with a 10% potassium carbonate solution and extracted twice with 50 ml of ethyl acetate each time. The organic phase is dried and then evaporated under reduced pressure, and the resulting precipitate is recrystallized from acetonitrile. Melting point: 220-224 C.
5
[ 104-53-0 ]
[ 56354-98-4 ]
6-(3-phenylpropyl)amino-2-benzothiazolone[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
EXAMPLE 8 6-(3-Phenylpropyl)amino-2-benzothiazolone By reaction of <strong>[56354-98-4]6-amino-2-benzothiazolone</strong> (1.66 g) with 3-phenylpropanal using the procedure of Example 1, the title compound (0.82 g) was prepared. m.p.: 145-149 C. IR(Nujol): 3400, 1650, 1610, 1590 cm-1. NMR (CDCl3): 1.70-2.20 (m, 2H), 2.50-3.30 (m, 4H), 4.10-4.50 (m, 1H), 6.30-7.00 (m, 3H), 7.20 (s, 5H), 10.70-11.20 (m, 1H).
6,7-dimethoxy-4-(2-oxo-2,3-dihydro-benzothiazol-6-ylamino)-quinoline-3-carbonitrile[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
With hydrogenchloride; pyridine hydrochloride; sodium carbonate; In water;
EXAMPLE 131 6,7-Dimethoxy-4-(2-oxo-2,3-dihydro-benzothiazol-6-ylamino)-quinoline-3-carbonitrile A mixture of 0.249 g of 4-chloro-6,7-dimethoxy-quinolin-3-carbonitrile, 0.166 g of <strong>[56354-98-4]6-amino-2-benzothiazolinone</strong>, 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.
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