2-bromo-N,N-dimethylpropanamide

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

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

Procedure: 5-(2,4-Dichlorophenoxy)-2-(propylthio)phenol (0.05 mole), potassium carbonate (0.2 mole), N,N-dimethyl 2-bromopropionamide (0.08 mole) and dimethylsulfoxide (200 ml) are charged into a 500 ml glass reaction flask equipped with a mechanical stirrer. The reaction mixture is stirred at room temperature for a period of about 8 hours. After this time the mixture is poured into 500 ml of water. The resulting mixture is extracted three times with 100 ml portions of methylene chloride. The extracts are then combined, washed with water and therafter dried. The dried solution is then stripped of solvent under reduced pressure to leave a residue. The residue is subjected to chromatography using a clay column and hexane/ethyl acetate mixtures as the eluant. The fractions containing the product are combined and stripped of solvent to yield the desired product N,N-dimethyl-2-[5-(2,4-dichlorophenoxy)-2-propylthiophenoxy]propionamide as the residue. equipped with a mechanical stirrer The resulting mixture is extracted three times with 100 ml portions of methylene chloride washed with water therafter dried to leave a residue The fractions containing the product

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

Procedure: 5-(2,4-Dichlorophenoxy)-2-(propylthio)phenol (0.05 mole), potassium carbonate (0.2 mole), N,N-dimethyl 2-bromopropionamide (0.08 mole) and dimethylsulfoxide (200 ml) are charged into a 500 ml glass reaction flask equipped with a mechanical stirrer. The reaction mixture is stirred at room temperature for a period of about 8 hours. After this time the mixture is poured into 500 ml of water. The resulting mixture is extracted three times with 100 ml portions of methylene chloride. The extracts are then combined, washed with water and therafter dried. The dried solution is then stripped of solvent under reduced pressure to leave a residue. The residue is subjected to chromatography using a clay column and hexane/ethyl acetate mixtures as the eluant. The fractions containing the product are combined and stripped of solvent to yield the desired product N,N-dimethyl-2-[5-(2,4-dichlorophenoxy)-2-propylthiophenoxy]propionamide as the residue. equipped with a mechanical stirrer The resulting mixture is extracted three times with 100 ml portions of methylene chloride washed with water therafter dried to leave a residue The fractions containing the product

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

Procedure: 5-(2,4-Dichlorophenoxy)-2-(propylthio)phenol (0.05 mole), potassium carbonate (0.2 mole), N,N-dimethyl 2-bromopropionamide (0.08 mole) and dimethylsulfoxide (200 ml) are charged into a 500 ml glass reaction flask equipped with a mechanical stirrer. The reaction mixture is stirred at room temperature for a period of about 8 hours. After this time the mixture is poured into 500 ml of water. The resulting mixture is extracted three times with 100 ml portions of methylene chloride. The extracts are then combined, washed with water and therafter dried. The dried solution is then stripped of solvent under reduced pressure to leave a residue. The residue is subjected to chromatography using a clay column and hexane/ethyl acetate mixtures as the eluant. The fractions containing the product are combined and stripped of solvent to yield the desired product N,N-dimethyl-2-[5-(2,4-dichlorophenoxy)-2-propylthiophenoxy]propionamide as the residue. equipped with a mechanical stirrer The resulting mixture is extracted three times with 100 ml portions of methylene chloride washed with water therafter dried to leave a residue The fractions containing the product

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

Procedure: 2-Bromo-5-chlorophenol (8 g), 2-bromo-N,N-dimethylpropionamide (6.66 g) and anhydrous potassium carbonate (2.6 g) in methyl iso-butyl ketone (100 ml) were refluxed with stirring overnight. The mixture was cooled to 50° and washed with 5% sodium hydroxide (2×20 ml) and then water (2×50 ml). The organic solution was dried and evaporated under reduced pressure to yield a pale red oil, which solidified on cooling. Recrystallisation from 50% aqueous ethanol gave the title compound, m.p. 76°-77°. Compounds 2, 9, 10 to 13, 17 and 21 were made by a similar procedure. The mixture was cooled to 50° washed with 5% sodium hydroxide (2×20 ml) The organic solution was dried evaporated under reduced pressure to yield a pale red oil, which on cooling Recrystallisation from 50% aqueous ethanol

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

Procedure: 2-Bromo-5-chlorophenol (8 g), 2-bromo-N,N-dimethylpropionamide (6.66 g) and anhydrous potassium carbonate (2.6 g) in methyl iso-butyl ketone (100 ml) were refluxed with stirring overnight. The mixture was cooled to 50° and washed with 5% sodium hydroxide (2×20 ml) and then water (2×50 ml). The organic solution was dried and evaporated under reduced pressure to yield a pale red oil, which solidified on cooling. Recrystallisation from 50% aqueous ethanol gave the title compound, m.p. 76°-77°. Compounds 2, 9, 10 to 13, 17 and 21 were made by a similar procedure. The mixture was cooled to 50° washed with 5% sodium hydroxide (2×20 ml) The organic solution was dried evaporated under reduced pressure to yield a pale red oil, which on cooling Recrystallisation from 50% aqueous ethanol

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

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

Procedure: In 100 ml of methyl ethyl ketone, 2.3 g of the intermediate of Preparation 1 of 2-(4-hydroxyphenoxy)quinoline, 1.8 g of N,N-dimethyl-α-bromopropionic acid amide and 1.4 g of potassium carbonate were added and the mixture was refluxed for 5 hours. After the reaction, the precipitated crystal was separated by a filtration and the solvent was distilled off and the product was dried under a reduced pressure. The resulting crude crystal was recrystallized from a solvent of methanol-water to obtain 3.6 g (yield 88%) of white crystal of the object compound. were added the mixture was refluxed for 5 hours After the reaction the precipitated crystal was separated by a filtration the solvent was distilled off the product was dried under a reduced pressure The resulting crude crystal was recrystallized from a solvent of methanol-water

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

Procedure: 5-(2,4-Dichlorophenoxy)-2-(propylthio)phenol (0.05 mole), potassium carbonate (0.2 mole), N,N-dimethyl 2-bromopropionamide (0.08 mole) and dimethylsulfoxide (200 ml) are charged into a 500 ml glass reaction flask equipped with a mechanical stirrer. The reaction mixture is stirred at room temperature for a period of about 8 hours. After this time the mixture is poured into 500 ml of water. The resulting mixture is extracted three times with 100 ml portions of methylene chloride. The extracts are then combined, washed with water and therafter dried. The dried solution is then stripped of solvent under reduced pressure to leave a residue. The residue is subjected to chromatography using a clay column and hexane/ethyl acetate mixtures as the eluant. The fractions containing the product are combined and stripped of solvent to yield the desired product N,N-dimethyl-2-[5-(2,4-dichlorophenoxy)-2-propylthiophenoxy]propionamide as the residue. equipped with a mechanical stirrer The resulting mixture is extracted three times with 100 ml portions of methylene chloride washed with water therafter dried to leave a residue The fractions containing the product

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

Procedure: 2-Bromo-5-chlorophenol (8 g), 2-bromo-N,N-dimethylpropionamide (6.66 g) and anhydrous potassium carbonate (2.6 g) in methyl iso-butyl ketone (100 ml) were refluxed with stirring overnight. The mixture was cooled to 50° and washed with 5% sodium hydroxide (2×20 ml) and then water (2×50 ml). The organic solution was dried and evaporated under reduced pressure to yield a pale red oil, which solidified on cooling. Recrystallisation from 50% aqueous ethanol gave the title compound, m.p. 76°-77°. Compounds 2, 9, 10 to 13, 17 and 21 were made by a similar procedure. The mixture was cooled to 50° washed with 5% sodium hydroxide (2×20 ml) The organic solution was dried evaporated under reduced pressure to yield a pale red oil, which on cooling Recrystallisation from 50% aqueous ethanol