Rubtsov, M. V. published the artcileDerivatives of sulfanilamide. IV, Application of Coumarin-6-sulfonyl chloride, the publication is Zhurnal Obshchei Khimii (1944), 857-64, database is CAplus.
6-Methoxy-2-chloroquinoline (25 g.) in 50 g. PhOH was heated to 135° and treated with dry NH3, cooled, treated with Me2CO, filtered and treated with EtOH-HCl, and the separated HCl salt neutralized to yield 6-methoxy-2-phenoxyquinoline, b3 183°, m. 46°. 6-Methoxy-2-chloroquinoline (17 g.) and 40 g. AcNH2 were heated to 180° for 4 h. and 200° for 2 h. with treatment with gaseous NH3; no reaction occurred; after addition of 1.7 g. CuCl and continuation of the reaction for 12 h. at 200° there was obtained 6.7 g. 6-methoxy-2-aminoquinoline, m. 175° (from water); 4 g. of this and 5.4 g. p-AcNHC6H4SO2Cl (I) in pyridine gave after 3 h. at 90-100° 2-(p-acetamidophenylsulfonamido)-6-methoxyquinoline, m. 245-6° (from 50% AcOH), which was hydrolyzed by 10% NaOH to 2-sulfanilamido-6-methoxyquinoline, m. 214.5° (from 50% AcOH). 4-Amino-6-methoxyquinoline (4 g.) and 5.4 g. I gave, as above, 2.4 g. 4-(p-acetamidophenylsulfonamido)-6-methoxyquinoline, m. 292° (from water), which was hydrolyzed by 10% NaOH to 4-sulfanilamido-6-methoxyquinoline, m. 274° (from 50% AcOH). 6-Aminoquinoline (7.2 g.) and 11.7 g. I gave 6-(p-acetamidophenylsulfonamido)quinoline, m. 282°, which was hydrolyzed by 17% HCl to 6-sulfanilamidoquinoline, m. 209-10° (from 50% EtOH). Coumarin (10 g.), added with cooling to 40 g. ClSO3H, heated to 100° for 4 h., cooled, and poured on ice yielded 10 g. 6-coumarinsulfonyl chloride, m. 116° (from (CH2Cl)2); treatment with 15% NH4OH at 35° gave 6-sulfamylcoumarin, m. 185° (from water), while substitution of sulfanilamide for NH4OH gave N-(p-sulfamylphenyl)-6-coumarin sulfonamide, m. 219° (from 50% EtOH), and the use of p-H2NC6H4CO2H gave p-carboxy-6-coumarinsulfonanilide, m. 241° (from 65% AcOH). Coumarinsulfonyl chloride and p-AcNHC6H4NH2 gave p-acetamido-6-coumarinsulfonanilide, m. 280° (from 75% AcOH), which was hydrolyzed by 10% NaOH to p-amino-6-coumarinsulfonanilide, m. 209° (from 50% EtOH). 6-Aminocoumarin (2.9 g.) with 2.4 g. I in Me2CO gave 3.5 g. 6-(p-acetamidophenylsulfonamido)coumarin, m. 230° (from 75% AcOH), which was hydrolyzed with 10% NaOH to 6-sulfanilamidocoumarin, m. 191° (from 50% EtOH). Only the last compound showed promising activity against streptococci, pneumococci, and staphylococci.
Zhurnal Obshchei Khimii published new progress about 10543-42-7. 10543-42-7 belongs to chlorides-buliding-blocks, auxiliary class Other Aromatic Heterocyclic,Chloride,Sulfonyl chlorides,Ester, name is Coumarin-6-sulfonyl chloride, and the molecular formula is C9H5ClO4S, Application of Coumarin-6-sulfonyl chloride.
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