N-(2-chloroethyl)methanesulfonamide

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 41 g (0.2 mole) of 1,4-dihydroxynaphthoic acid was dissolved in 200 ml DMF, into which was added dropwise 80 g of a 28% methanol solution of sodium methoxide (0.4 mole) and bubbling nitrogen therethrough at room temperature. Then, while controlling the reaction temperature between 35°-40° C., 25.2 g (0.16 mole) of β-methanesulfonamidoethyl chloride was added and the mixture was stirred for 1 hour. Finally, the solution was poured into a mixture of 100 ml of concentrated (36%) hydrochloric acid and 500 ml of water to separate a crystalline product, which was filtered. The crystalline product was purified by refluxing with methanol and, thus, 20.8 g of 1-hydroxy-4-(β-methanesulfonamidoethoxy)-2-naphthoic acid was obtained with a yield of 40%. bubbling nitrogen at room temperature between 35°-40° C. Finally, the solution was poured into a mixture of 100 ml of concentrated (36%) hydrochloric acid and 500 ml of water to separate a crystalline product, which was filtered The crystalline product was purified by refluxing with methanol

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 41 g (0.2 mole) of 1,4-dihydroxynaphthoic acid was dissolved in 200 ml DMF, into which was added dropwise 80 g of a 28% methanol solution of sodium methoxide (0.4 mole) and bubbling nitrogen therethrough at room temperature. Then, while controlling the reaction temperature between 35°-40° C., 25.2 g (0.16 mole) of β-methanesulfonamidoethyl chloride was added and the mixture was stirred for 1 hour. Finally, the solution was poured into a mixture of 100 ml of concentrated (36%) hydrochloric acid and 500 ml of water to separate a crystalline product, which was filtered. The crystalline product was purified by refluxing with methanol and, thus, 20.8 g of 1-hydroxy-4-(β-methanesulfonamidoethoxy)-2-naphthoic acid was obtained with a yield of 40%. bubbling nitrogen at room temperature between 35°-40° C. Finally, the solution was poured into a mixture of 100 ml of concentrated (36%) hydrochloric acid and 500 ml of water to separate a crystalline product, which was filtered The crystalline product was purified by refluxing with methanol

Conditions: temp:150.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 22.9 g (0.1 mol) of 5,6-dichloro-1-ethyl-2-methylbenzoimidazole and 23.6 g (0.15 mol) of N-(2-chloroethyl)methanesulfonamide were put into a 200-ml three-necked flask equipped with a stirrer and heated with stirring for 2 hours on an oil bath which had been heated to a temperature of 150° C. Then, 20 ml of anisole was added to the mixture. The mixture was then allowed to cool to room temperature with stirring. The resulting crystals were filtered off, washed with acetone and isopropanol, and dried. equipped with a stirrer heated to cool to room temperature with stirring The resulting crystals were filtered off washed with acetone and isopropanol dried

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 7g of 4-(N-p-toluenesulfonyl)amino-3-methyl-N-ethylaniline, 4g of β-methanesulfonamidoethyl chloride, 2.1g of sodium hydrogen carbonate, 16g of water and 30ml of methanol were refluxed for 5 hours, and then 16g of sulfuric acid were added thereto and the entire reaction system was again refluxed. Next, the reaction solution was condensed to half the original volume and 300ml of isopropyl alcohol were added thereto to separate crystals. The crystals were filtered out and dried to obtain 1.5g of 4-amino-3-methyl-N-(β-methanesulfonamidoethyl)-N-ethylaniline. sesquisulfate. H2O. were refluxed for 5 hours the entire reaction system was again refluxed were added to separate crystals The crystals were filtered out dried

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 57.6g of 4-acetamino-3-methyl-N-ethylaniline, 52g of βmethanesulfonamidoethyl chloride, 27.7g of sodium hydrogen carbonate, 70g of water and 70ml of methanol were refluxed for 5 hours, and thereafter the methanol was distilled out under reduced pressure. Water was added to the reaction system and an oily product separated out. This oily product was poured into ethyl acetate and cooled to obtain white 4-acetamino-3-methyl-N-(β-methanesulfonamidoethyl)-N-ethylaniline. were refluxed for 5 hours the methanol was distilled out under reduced pressure Water was added to the reaction system an oily product separated out This oily product was poured into ethyl acetate cooled

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 41 g (0.2 mole) of 1,4-dihydroxynaphthoic acid was dissolved in 200 ml DMF, into which was added dropwise 80 g of a 28% methanol solution of sodium methoxide (0.4 mole) and bubbling nitrogen therethrough at room temperature. Then, while controlling the reaction temperature between 35°-40° C., 25.2 g (0.16 mole) of β-methanesulfonamidoethyl chloride was added and the mixture was stirred for 1 hour. Finally, the solution was poured into a mixture of 100 ml of concentrated (36%) hydrochloric acid and 500 ml of water to separate a crystalline product, which was filtered. The crystalline product was purified by refluxing with methanol and, thus, 20.8 g of 1-hydroxy-4-(β-methanesulfonamidoethoxy)-2-naphthoic acid was obtained with a yield of 40%. bubbling nitrogen at room temperature between 35°-40° C. Finally, the solution was poured into a mixture of 100 ml of concentrated (36%) hydrochloric acid and 500 ml of water to separate a crystalline product, which was filtered The crystalline product was purified by refluxing with methanol

Conditions: temp:150.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 22.9 g (0.1 mol) of 5,6-dichloro-1-ethyl-2-methylbenzoimidazole and 23.6 g (0.15 mol) of N-(2-chloroethyl)methanesulfonamide were put into a 200-ml three-necked flask equipped with a stirrer and heated with stirring for 2 hours on an oil bath which had been heated to a temperature of 150° C. Then, 20 ml of anisole was added to the mixture. The mixture was then allowed to cool to room temperature with stirring. The resulting crystals were filtered off, washed with acetone and isopropanol, and dried. equipped with a stirrer heated to cool to room temperature with stirring The resulting crystals were filtered off washed with acetone and isopropanol dried

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 7g of 4-(N-p-toluenesulfonyl)amino-3-methyl-N-ethylaniline, 4g of β-methanesulfonamidoethyl chloride, 2.1g of sodium hydrogen carbonate, 16g of water and 30ml of methanol were refluxed for 5 hours, and then 16g of sulfuric acid were added thereto and the entire reaction system was again refluxed. Next, the reaction solution was condensed to half the original volume and 300ml of isopropyl alcohol were added thereto to separate crystals. The crystals were filtered out and dried to obtain 1.5g of 4-amino-3-methyl-N-(β-methanesulfonamidoethyl)-N-ethylaniline. sesquisulfate. H2O. were refluxed for 5 hours the entire reaction system was again refluxed were added to separate crystals The crystals were filtered out dried

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 57.6g of 4-acetamino-3-methyl-N-ethylaniline, 52g of βmethanesulfonamidoethyl chloride, 27.7g of sodium hydrogen carbonate, 70g of water and 70ml of methanol were refluxed for 5 hours, and thereafter the methanol was distilled out under reduced pressure. Water was added to the reaction system and an oily product separated out. This oily product was poured into ethyl acetate and cooled to obtain white 4-acetamino-3-methyl-N-(β-methanesulfonamidoethyl)-N-ethylaniline. were refluxed for 5 hours the methanol was distilled out under reduced pressure Water was added to the reaction system an oily product separated out This oily product was poured into ethyl acetate cooled