(cinnamylideneamino)thiourea

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

Procedure: The compound is prepared according to the method described in example 1B from cinnamaldehyde thiosemicarbazone (0.28 mmoles) (Eur. J. Med. Chem. 25(7), 581-588, 1990) and from 2-bromo-4′-hydroxy-2′-methylacetophenone (0.28 mmoles). Yield 36%. The compound is prepared

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

Procedure: The compound is prepared according to the method described in Example 1B from cinnamaldehyde thiosemicarbazone (0.5 mmol) (Eur. J. Med. Chem. 25(7), 581-588, 1990) and from 2-bromo-4′-trifluoromethylacetophenone (0.5 mmol) (Tet., 59(8) 1317-1325, 2003). Yield 42%. The compound is prepared

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

Procedure: A mixture of 70.0 g (0.35 m) of cinnamaldehyde thiosemicarbazone and 56.0 g (1.16 m) of ferric ammonium sulfate dodecahydrate was pulverized with a mortar and pestle and added portionwise to 1400 ml of hot water. The mixture was stirred at 60°-100° C. for 11/4 hr., during which time the color of the mixture changed from yellow-orange to dark red and much of the solid material went into solution. The mixture was filtered hot to yield 54.5 g of a brown granular product. The mother liquors were cooled under refrigeration and refiltered to give another 12.3 g of product. The crude product was pulverized and triturated twice with chloroform to remove the residual starting material and the dark brown impurities from the product, leaving 27.4 g of a beige microcrystalline powder. An additional 4.60 g of product was recovered by concentrating the chloroform filtrate. Total yield was 32.0 g (0.16 m), mp. 212°-214° C. (dec.). This procedure is novel and is of general utility for preparing these types of compounds. The novel procedure for this particular product is defined as: The mixture was filtered hot

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

Procedure: A solution of 18.2 g (0.20 m) of thiosemicarbazide in 250 ml of hot water was gradually added to a solution of 26.4 g (0.20 m) of cinnamaldehyde in 250 ml of hot 2B ethanol. Small, colorless crystals began to ppt from the homogeneous mixture after several minutes of heating on a steam bath. Heating was continued for a half an hour, after which the mixture was cooled to room temperature and the product was collected by filtration, washed with cold ethanol, and air-dried to yield 25.5 g of small, pale yellow crystals. An additional 18.3 g of product was recovered by concentrating the mother liquors. Recrystallization from ethanol gave 29.3 g (0.14 m) of small, pale yellow crystals, m.p. 137°-139° C. to ppt from the homogeneous mixture after several minutes of heating on a steam bath Heating was continued for a half an hour the product was collected by filtration washed with cold ethanol air-dried to yield 25.5 g of small, pale yellow crystals An additional 18.3 g of product was recovered by concentrating the mother liquors Recrystallization from ethanol gave 29.3 g (0.14 m) of small, pale yellow crystals, m.p. 137°-139° C.

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

Procedure: A mixture of 70.0 g (0.35 m) of cinnamaldehyde thiosemicarbazone and 56.0 g (1.16 m) of ferric ammonium sulfate dodecahydrate was pulverized with a mortar and pestle and added portionwise to 1400 ml of hot water. The mixture was stirred at 60°-100° C. for 11/4 hr., during which time the color of the mixture changed from yellow-orange to dark red and much of the solid material went into solution. The mixture was filtered hot to yield 54.5 g of a brown granular product. The mother liquors were cooled under refrigeration and refiltered to give another 12.3 g of product. The crude product was pulverized and triturated twice with chloroform to remove the residual starting material and the dark brown impurities from the product, leaving 27.4 g of a beige microcrystalline powder. An additional 4.60 g of product was recovered by concentrating the chloroform filtrate. Total yield was 32.0 g (0.16 m), mp. 212°-214° C. (dec.). This procedure is novel and is of general utility for preparing these types of compounds. The novel procedure for this particular product is defined as: The mixture was filtered hot

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

Procedure: A solution of 18.2 g (0.20 m) of thiosemicarbazide in 250 ml of hot water was gradually added to a solution of 26.4 g (0.20 m) of cinnamaldehyde in 250 ml of hot 2 B ethanol. Small, colorless crystals began to ppt from the homogeneous mixture after several minutes of heating on a steam bath. Heating was continued for a half an hour, after which the mixture was cooled to room temperature and the product was collected by filtraton, washed with cold ethanol, and air-dried to yield 25.5 g of small, pale yellow crystals. An additional 18.3 g of product was recovered by concentrating the mother liquors. Recrystallization from ethanol gave 29.3 g (0.14 m) of small, pale yellow crystals, m.p. 137°-139° C. to ppt from the homogeneous mixture after several minutes of heating on a steam bath Heating was continued for a half an hour the product was collected by filtraton washed with cold ethanol air-dried to yield 25.5 g of small, pale yellow crystals An additional 18.3 g of product was recovered by concentrating the mother liquors Recrystallization from ethanol gave 29.3 g (0.14 m) of small, pale yellow crystals, m.p. 137°-139° C.