hexadecyl(trimethyl)azanium;hydroxide

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

Procedure: The last third of the cetyl-trimethylammonium hydroxide solution is neutralized with 12.39 g of 4-ethoxy-2-hydroxy-benzoic acid (the equivalent weight of which has been determined as 185.8 by titration with 0.1N sodium hydroxide solution) by scattering in as a powder. The resulting yellow solution in methanol is concentrated to dryness. 31.1 g of a slightly brownish residue are obtained, which can be purified by recrystallization from 300 ml of ethyl acetate several times. Cetyl-trimethylammonium 4-ethoxysalicylate is obtained in (slightly reddish) crystals (titration with perchloric acid in glacial acetic acid gives the expected equivalent weight). The resulting yellow solution in methanol is concentrated to dryness 31.1 g of a slightly brownish residue are obtained which can be purified by recrystallization from 300 ml of ethyl acetate several times

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

Procedure: The last third of the cetyl-trimethylammonium hydroxide solution is neutralized with 12.39 g of 4-ethoxy-2-hydroxy-benzoic acid (the equivalent weight of which has been determined as 185.8 by titration with 0.1N sodium hydroxide solution) by scattering in as a powder. The resulting yellow solution in methanol is concentrated to dryness. 31.1 g of a slightly brownish residue are obtained, which can be purified by recrystallization from 300 ml of ethyl acetate several times. Cetyl-trimethylammonium 4-ethoxysalicylate is obtained in (slightly reddish) crystals (titration with perchloric acid in glacial acetic acid gives the expected equivalent weight). The resulting yellow solution in methanol is concentrated to dryness 31.1 g of a slightly brownish residue are obtained which can be purified by recrystallization from 300 ml of ethyl acetate several times

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

Procedure: The last third of the cetyl-trimethylammonium hydroxide solution is neutralized with 12.39 g of 4-ethoxy-2-hydroxy-benzoic acid (the equivalent weight of which has been determined as 185.8 by titration with 0.1N sodium hydroxide solution) by scattering in as a powder. The resulting yellow solution in methanol is concentrated to dryness. 31.1 g of a slightly brownish residue are obtained, which can be purified by recrystallization from 300 ml of ethyl acetate several times. Cetyl-trimethylammonium 4-ethoxysalicylate is obtained in (slightly reddish) crystals (titration with perchloric acid in glacial acetic acid gives the expected equivalent weight). The resulting yellow solution in methanol is concentrated to dryness 31.1 g of a slightly brownish residue are obtained which can be purified by recrystallization from 300 ml of ethyl acetate several times

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

Procedure: In a similar manner to Example 10, piretanide can be reacted with cetyltrimethylammonium hydroxide in water to yield cetyltrimethylammonium 3-aminosulfonyl-4-phenoxy-5-(1-pyrrolidinyl)benzoate.

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

Procedure: In similar manner to Example 10, furosemide can be reacted with cetyltrimethylammonium hydroxide in water to yield cetyltrimethylammonium 5-aminosulfonyl-4-chloro-2-[(2-furanylmethyl)amino]benzoate.

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

Procedure: In a similar manner to Example 9, bumetanide can be reacted with cetyltrimethylammonium hydroxide in water to yield cetyltrimethylammonium 3-aminosulfonyl-5-butylamino-4-phenoxybenzoate.

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

Procedure: The last third of the cetyl-trimethylammonium hydroxide solution is neutralized with 12.39 g of 4-ethoxy-2-hydroxy-benzoic acid (the equivalent weight of which has been determined as 185.8 by titration with 0.1N sodium hydroxide solution) by scattering in as a powder. The resulting yellow solution in methanol is concentrated to dryness. 31.1 g of a slightly brownish residue are obtained, which can be purified by recrystallization from 300 ml of ethyl acetate several times. Cetyl-trimethylammonium 4-ethoxysalicylate is obtained in (slightly reddish) crystals (titration with perchloric acid in glacial acetic acid gives the expected equivalent weight). The resulting yellow solution in methanol is concentrated to dryness 31.1 g of a slightly brownish residue are obtained which can be purified by recrystallization from 300 ml of ethyl acetate several times