butanethioamide

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A mixture of 20.6 g of ethyl 2-bromo-4-oxo-butyrate, 10.9 g of thiobutyramide and 400 ml of dichloroethane was refluxed under a nitrogen atmosphere which recycling the dehydrated condensate. The mixture was cooled and then mixed with 45 ml of a saturated sodium bicarbonate aqueous solution. The mixture was decanted and the organic phase was dried and evaporated to dryness. The liquid residue was chromatographed over silica gel and elution with a 8-2 cyclohexane-benzene mixture yielded 15.4 g of ethyl 2-propyl-5-thiazole-acetate. The IR spectrum in CHCl3 showed an ester carbonyl at 1737cm-1 and C=C at 1536cm-1 was refluxed under a nitrogen atmosphere which The mixture was cooled The mixture was decanted the organic phase was dried evaporated to dryness The liquid residue was chromatographed over silica gel and elution with a 8-2 cyclohexane-benzene mixture

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A mixture of 20.6 g of ethyl 2-bromo-4-oxo-butyrate, 10.9 g of thiobutyramide and 400 ml of dichloroethane was refluxed under a nitrogen atmosphere which recycling the dehydrated condensate. The mixture was cooled and then mixed with 45 ml of a saturated sodium bicarbonate aqueous solution. The mixture was decanted and the organic phase was dried and evaporated to dryness. The liquid residue was chromatographed over silica gel and elution with a 8-2 cyclohexane-benzene mixture yielded 15.4 g of ethyl 2-propyl-5-thiazole-acetate. The IR spectrum in CHCl3 showed an ester carbonyl at 1737cm-1 and C=C at 1536cm-1 was refluxed under a nitrogen atmosphere which The mixture was cooled The mixture was decanted the organic phase was dried evaporated to dryness The liquid residue was chromatographed over silica gel and elution with a 8-2 cyclohexane-benzene mixture

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: Ethyl 3-bromo-2-oxopropanoate (6.32 mL) was added to a solution of butanethioamide (example 87, step a) (5.2 g) in ethanol (100 mL) and the resulting mixture heated at reflux overnight. The solvent was evaporated and the residue partitioned between ethyl acetate (100 mL) and saturated sodium hydrogen carbonate solution (100 mL). The layers were separated and the aqueous phase extracted with ethyl acetate (2×100 mL). The combined organic solutions were washed with brine (100 mL) dried over sodium sulphate, filtered and evaporated. Purification was by silica gel chromatography eluting with 10:1 isohexane:ethyl acetate. The fractions containing product were combined and evaporated to give the subtitled compound as a yellow oil. Yield 5.24 g. the resulting mixture heated at reflux overnight The solvent was evaporated the residue partitioned between ethyl acetate (100 mL) and saturated sodium hydrogen carbonate solution (100 mL) The layers were separated the aqueous phase extracted with ethyl acetate (2×100 mL) The combined organic solutions were washed with brine (100 mL) dried over sodium sulphate filtered evaporated Purification eluting with 10:1 isohexane The fractions containing product evaporated

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: Ethyl 3-bromo-2-oxopropanoate (6.32 mL) was added to a solution of butanethioamide (example 87, step a) (5.2 g) in ethanol (100 mL) and the resulting mixture heated at reflux overnight. The solvent was evaporated and the residue partitioned between ethyl acetate (100 mL) and saturated sodium hydrogen carbonate solution (100 mL). The layers were separated and the aqueous phase extracted with ethyl acetate (2×100 mL). The combined organic solutions were washed with brine (100 mL) dried over sodium sulphate, filtered and evaporated. Purification was by silica gel chromatography eluting with 10:1 isohexane:ethyl acetate. The fractions containing product were combined and evaporated to give the subtitled compound as a yellow oil. Yield 5.24 g. the resulting mixture heated at reflux overnight The solvent was evaporated the residue partitioned between ethyl acetate (100 mL) and saturated sodium hydrogen carbonate solution (100 mL) The layers were separated the aqueous phase extracted with ethyl acetate (2×100 mL) The combined organic solutions were washed with brine (100 mL) dried over sodium sulphate filtered evaporated Purification eluting with 10:1 isohexane The fractions containing product evaporated

反応条件: temp:60.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A mixture of 38 g of thiobutyramide, 54.2 g of ethyl 2-formyl-2-chloro-acetate, 185 ml of dioxane and 22 g of magnesium carbonate was heated for 4 hours at 60°C and the precipitate formed was removed by filtration. The dioxane was distilled from the filtrate and the residue was taken up in 665 ml of a 1-1 ethyl ether-water mixture. The ether phase was recovered by decantation and was washed with aqueous 10% hydrochloric acid solution and then with water until the wash waters were neutral, dried over magnesium sulfate and distilled to dryness. The residue was distilled to obtain 57 g of ethyl 2-n-propylthiazol-5-carboxylate boiling at 95°-106°C under 0.5 mm Hg. the precipitate formed was removed by filtration The dioxane was distilled from the filtrate The ether phase was recovered by decantation was washed with aqueous 10% hydrochloric acid solution dried over magnesium sulfate distilled to dryness The residue was distilled

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A mixture of 20.6 g of ethyl 2-bromo-4-oxo-butyrate, 10.9 g of thiobutyramide and 400 ml of dichloroethane was refluxed under a nitrogen atmosphere which recycling the dehydrated condensate. The mixture was cooled and then mixed with 45 ml of a saturated sodium bicarbonate aqueous solution. The mixture was decanted and the organic phase was dried and evaporated to dryness. The liquid residue was chromatographed over silica gel and elution with a 8-2 cyclohexane-benzene mixture yielded 15.4 g of ethyl 2-propyl-5-thiazole-acetate. The IR spectrum in CHCl3 showed an ester carbonyl at 1737cm-1 and C=C at 1536cm-1 was refluxed under a nitrogen atmosphere which The mixture was cooled The mixture was decanted the organic phase was dried evaporated to dryness The liquid residue was chromatographed over silica gel and elution with a 8-2 cyclohexane-benzene mixture

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: Ethyl 3-bromo-2-oxopropanoate (6.32 mL) was added to a solution of butanethioamide (example 87, step a) (5.2 g) in ethanol (100 mL) and the resulting mixture heated at reflux overnight. The solvent was evaporated and the residue partitioned between ethyl acetate (100 mL) and saturated sodium hydrogen carbonate solution (100 mL). The layers were separated and the aqueous phase extracted with ethyl acetate (2×100 mL). The combined organic solutions were washed with brine (100 mL) dried over sodium sulphate, filtered and evaporated. Purification was by silica gel chromatography eluting with 10:1 isohexane:ethyl acetate. The fractions containing product were combined and evaporated to give the subtitled compound as a yellow oil. Yield 5.24 g. the resulting mixture heated at reflux overnight The solvent was evaporated the residue partitioned between ethyl acetate (100 mL) and saturated sodium hydrogen carbonate solution (100 mL) The layers were separated the aqueous phase extracted with ethyl acetate (2×100 mL) The combined organic solutions were washed with brine (100 mL) dried over sodium sulphate filtered evaporated Purification eluting with 10:1 isohexane The fractions containing product evaporated