S-(3-chloro-3-oxopropyl) ethanethioate

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

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

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

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

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

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

Procedure: The solution of 0.052 g of 3-acetylthiopropanoyl chloride in 1 ml of methylene chloride is added slowly to the mixture of 60 mg of 3,3-dimethylindoline-2-carboxamide, 87 mg of potassium carbonate and 9 ml of methylene chloride. The mixture is stirred at room temperature overnight, diluted with methylene chloride and filtered. The filtrate is washed with saturated aqueous sodium bicarbonate, water, 0.5N hydrochloric acid and water, dried, evaporated and the residue crystallized from diethyl ether, to yield the 1-(3-acetylthiopropanoyl)-3,3-dimethylindoline-2-carboxamide melting at 156°-158°. filtered The filtrate is washed with saturated aqueous sodium bicarbonate, water, 0.5N hydrochloric acid and water dried evaporated the residue crystallized from diethyl ether

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

Procedure: 0.93 g of triethylamine are added to the suspension of 0.7 g of 3,3-dimethylindoline-2-carboxylic acid hydrochloride in 20 ml of methylene chloride and the resulting solution is cooled to -10°. The solution of 0.51 g of 3-acetylthiopropanoyl chloride in 5 ml of methylene chloride is added dropwise and the mixture stirred at -5° to -10° for 1 hour and at room temperature for 3 hours. It is cooled to 0° and treated with 10 ml of 3N hydrochloric acid. The organic layer is separated and the aqueous solution further extracted with methylene chloride. The combined methylene chloride solutions are dried and evaporated, to give the 1-(3-acetylthiopropanoyl)-3,3-dimethylindoline-2-carboxylic acid as a foam. the resulting solution is cooled to -10° It is cooled to 0° The organic layer is separated the aqueous solution further extracted with methylene chloride The combined methylene chloride solutions are dried evaporated

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

Procedure: The solution of 3.6 g of 3-acetylthiopropanoyl chloride in 10 ml of methylene chloride is added dropwise while stirring under nitrogen to the suspension of 5.4 g of 5,6-dimethoxyindoline-2-carboxylic acid ethyl ester and 5.96 g of powdered potassium carbonate in 40 ml of methylene chloride. The mixture is stirred for 2 hours at room temperature, filtered and the filtrate washed successively with saturated aqueous sodium bicarbonate, water, 0.5N hydrochloric acid and water. The organic solution is dried, evaporated, the residue crystallized from petroleum ether and further purified by slurrying in diethyl ether for 2 hours, to yield the 1-(3-acetylthiopropanoyl)-5,6-dimethoxyindoline-2-carboxylic acid ethyl ester melting at 104°-106°. filtered the filtrate washed successively with saturated aqueous sodium bicarbonate, water, 0.5N hydrochloric acid and water The organic solution is dried evaporated the residue crystallized from petroleum ether further purified by slurrying in diethyl ether for 2 hours

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

Procedure: The solution of 3.6 g of 3-acetylthiopropanoyl chloride in 10 ml of methylene chloride is added dropwise while stirring under nitrogen to the suspension of 5.4 g of 5,6-dimethoxyindoline-2-carboxylic acid ethyl ester and 5.96 g of powdered potassium carbonate in 40 ml of methylene chloride. The mixture is stirred for 2 hours at room temperature, filtered and the filtrate washed successively with saturated aqueous sodium bicarbonate, water, 0.5N hydrochloric acid and water. The organic solution is dried, evaporated, the residue crystallized from petroleum ether and further purified by slurrying in diethyl ether for 2 hours, to yield the 1-(3-acetylthiopropanoyl)-5,6-dimethoxyindoline-2-carboxylic acid ethyl ester melting at 104°-106°. filtered the filtrate washed successively with saturated aqueous sodium bicarbonate, water, 0.5N hydrochloric acid and water The organic solution is dried evaporated the residue crystallized from petroleum ether further purified by slurrying in diethyl ether for 2 hours

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

Procedure: To the mixture of 7.8 g of powdered potassium carbonate, 5.0 g of indoline-2-carboxylic acid methyl ester and 50 ml of methylene chloride, 4.7 g of 3-acetylthiopropanoyl chloride [Helv. Chim. Acta 40, 2148 (1957)] in 10 ml of methylene chloride are added at room temperature. After 1 hour the mixture is diluted with 100 ml of methylene chloride and washed with 50 ml of water, 50 ml of 1N hydrochloric acid and 50 ml of saturated aqueous sodium bicarbonate. The organic layer is dried and evaporated, to give the 1-(3-acetylthiopropanoyl)-indoline-2-carboxylic acid methyl ester as an oil, showing IR-bands at 1710, 1690 and 1640 cm-1. are added at room temperature washed with 50 ml of water, 50 ml of 1N hydrochloric acid and 50 ml of saturated aqueous sodium bicarbonate The organic layer is dried evaporated

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

Procedure: (±)-3-(2-Pyridyl)-4,5-dihydro-1H-pyrazole-5-carboxylic acid (3.82 g) is dissolved in 100 ml of water containing 2.12 g of sodium bicarbonate at 10° C. 3-(Acetylthio)propionyl chloride (3.9 g) in 15 ml of ether and 20% sodium carbonate solution are added simultaneously; the pH is maintained between 7.5 and 8.5. The reaction mixture is then stirred at room temperature for 2 hours and extracted with ether (discarded). The aqueous layer is acidified with acetic acid and extracted with ethyl acetate three times. The solvent is dried over anhydrous magnesium sulfate and concentrated in vacuo, yielding the title compound. the pH is maintained between 7.5 and 8.5 extracted with ether (discarded) extracted with ethyl acetate three times The solvent is dried over anhydrous magnesium sulfate concentrated in vacuo

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

Procedure: (±)-4,5-Dihydro-3-(2-thienyl)-1H-pyrazole-5-carboxylic acid is dissolved in aqueous Na2CO3 (1.38 g) at pH 8.6. The temperature is lowered to 5° C. and 3-(acetylthio)propionyl chloride (4.15 g) and a 25% solution of Na2CO3 are added simultaneously maintaining the pH at 8-9. The final pH is 8.9 and the reaction is stirred for 2 hours at room temperature. It is then extracted with ethyl acetate and the ethyl acetate is discarded. The aqueous layer is made strongly acid with 20% HCl and the gummy precipitate is extracted with ethyl acetate. The ethyl acetate is dried over MgSO4 and removed to yield a viscous residue (7.2 g) which is triturated with ether to yield 5.1 g of material, melting point 127°-130° C., dec. After recrystallization from CH3CN (very soluble) the melting point is constant at 134°-136° C., dec. is lowered to 5° C. maintaining the pH at 8-9 It is then extracted with ethyl acetate the gummy precipitate is extracted with ethyl acetate The ethyl acetate is dried over MgSO4 removed