5-propan-2-ylcyclohexane-1,3-dione

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: Reaction of equimolar amounts of 5-isopropyl1,3-cyclohexanedione with benzenesulfonylisocyanate in benzene according to the procedure of Example 1 affords 5-ISOPROPYL-2-(N-BENZENESULFONYLCARBAMOYL)-1,3-CYCLOHEXANEDIONE, m.p. 112.5°-114° C. (corr.).

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

Procedure: Reaction of equimolar amounts of 5-isopropyl1,3-cyclohexanedione with benzenesulfonylisocyanate in benzene according to the procedure of Example 1 affords 5-ISOPROPYL-2-(N-BENZENESULFONYLCARBAMOYL)-1,3-CYCLOHEXANEDIONE, m.p. 112.5°-114° C. (corr.).

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

Procedure: Reaction of equimolar amounts of 5-isopropyl-1,3-cyclohexanedione with p-chlorobenzenesulfonylisocyanate in benzene according to the procedure of Example 1 affords 2-(N-p-CHLOROBENZENESULFONYLCARBAMOYL)-5-ISOPROPYL-1,3-CYCLOHEXANEDIONE, m.p. 100.5°-101.5° C. (resolidified and melting at 183.5° C. with dec.)(corr.).

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

Procedure: Reaction of 5-isopropyl-1,3-cyclohexanedione with p-toluenesulfonylisocyanate in benzene according to the procedure of Example 1 affords 5-ISOPROPYL-2-(N-p-TOLUENESULFONYLCARBAMOYL)-1,3-CYCLOHEXANEDIONE, m.p. 106.5°-107.5° C. (corr.).

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

Procedure: To a fresh solution of sodium ethoxide prepared from 23 g (1.0 mole) of sodium and 700 ml of absolute ethanol is added 168.2 g (1.05 mole) of diethyl malonate and 114.24 g (1.02 mole) of distilled 5-methyl-3-hexene-2-one. The mixture is refluxed for 1 hour; an additional 125 ml of ethanol added; and refluxing continued for two more hours. A solution of 123.4 g of potassium hydroxide in a 600 ml of water is then added and the reaction mixture refluxed for 6 hours. The mixture is then neutralized with 12% hydrochloric acid to pH 4. The ethanol is distilled and the mixture treated with three 15 g portions of activated charcoal. The hot reaction mixture is filtered through filter aid after acidification to pH 2. The product is extracted with hot isopropyl ether (700 ml). Cooling of the isopropyl ether layer results in 60.5 g (40% yield) of the product, m.p. 52°- 65° C. The mixture is refluxed for 1 hour and refluxing the reaction mixture refluxed for 6 hours The ethanol is distilled the mixture treated with three 15 g portions of activated charcoal The hot reaction mixture is filtered through filter aid after acidification to pH 2 The product is extracted with hot isopropyl ether (700 ml) Cooling of the isopropyl ether layer

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

Procedure: To a fresh solution of sodium ethoxide prepared from 23 g (1.0 mole) of sodium and 700 ml of absolute ethanol is added 168.2 g (1.05 mole) of diethyl malonate and 114.24 g (1.02 mole) of distilled 5-methyl-3-hexene-2-one. The mixture is refluxed for 1 hour; an additional 125 ml of ethanol added; and refluxing continued for two more hours. A solution of 123.4 g of potassium hydroxide in a 600 ml of water is then added and the reaction mixture refluxed for 6 hours. The mixture is then neutralized with 12% hydrochloric acid to pH 4. The ethanol is distilled and the mixture treated with three 15 g portions of activated charcoal. The hot reaction mixture is filtered through filter aid after acidification to pH 2. The product is extracted with hot isopropyl ether (700 ml). Cooling of the isopropyl ether layer results in 60.5 g (40% yield) of the product, m.p. 52°- 65° C. The mixture is refluxed for 1 hour and refluxing the reaction mixture refluxed for 6 hours The ethanol is distilled the mixture treated with three 15 g portions of activated charcoal The hot reaction mixture is filtered through filter aid after acidification to pH 2 The product is extracted with hot isopropyl ether (700 ml) Cooling of the isopropyl ether layer

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

Procedure: A mixture of 2-benzylthio-4,5-dihydro-1H-imidazole (15.4 grams, 0.08 mole), 5-(1-methylethyl)-1,3-cyclohexanedione (12.3 grams, 0.08 mole) and 0.11 gram of DABCO is heated at 115°-120° C., with stirring, for a period of 7.1 hours. The cooled residue is dissolved in dichloromethane and the solution extracted with three portions of 3N sodium hydroxide, then with four portions of 3N hydrochloric acid. The organic phase is then dried over magnesium sulfate and evaporated, to give 15.31 grams of crude product as a yellow solid. The material is recrystallized twice from toluene and once from ethyl acetate, to give 2.58 grams of product, m.p. 223°-225° C. is heated at 115°-120° C. the solution extracted with three portions of 3N sodium hydroxide The organic phase is then dried over magnesium sulfate evaporated to give 15.31 grams of crude product as a yellow solid The material is recrystallized twice from toluene and once from ethyl acetate