1,3-diphenylthiourea

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: To a 2 l flask were added 342 g of thiocarbanilide, 240 g of methyl iodide and 350 cc of ethanol and the mixture was refluxed for 2 hours. After cooling the mixture to a room temperature, a small amount of water was added and the mixture was allowed to stand to precipitate the raw product, which was then filtered off and dissolved in 12 l of hot water. After filtration, the filtrate was converted to an alkaline solution by addition of NaOH to precipitate the product. The product was filtered and washed well until the filtrate became neutral. After drying, the product was recrystalized in 1 l of ethanol to give S-methyl-N,N'-diphenylisothiourea. the mixture was refluxed for 2 hours to precipitate the raw product, which was then filtered off dissolved in 12 l of hot water After filtration the filtrate was converted to an alkaline solution by addition of NaOH to precipitate the product The product was filtered washed well until the filtrate After drying the product was recrystalized in 1 l of ethanol

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

Procedure: 1,3-Diphenylthiourea (22.8 g), triphenylphosphine (10.1 g) triethylamine (10.1 g) and carbon tetrachloride (21.6 g) were refluxed for 4 hours in methylene chloride (300 ml). The solvent was removed under vacuum. The residue was shaken with hexane (300 ml); the hexane solution was evaporated and the residue was distilled to afford the title compound as an oil bp 115°-120°/0.3 mm. Similarly, by using this procedure, but employing other 1,3-disubstituted thioureas instead of 1,3-diphenylthiourea, other carbodiimides can be made. The solvent was removed under vacuum the hexane solution was evaporated the residue was distilled

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

Procedure: A mixture of 22.8 gm. (0.1 mole) of thiocarbanilide and 17 gm. (0.12 mole) of methyl iodide in 400 ml. of ethanol is heated at reflux for 6 hours. The solvent is evaporated and residue is crystallized from ethyl acetate; 29 gm. (78%), m.p. 155°-156°. A mixture of 22.8 gm at reflux for 6 hours The solvent is evaporated residue is crystallized from ethyl acetate

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

Procedure: 1.45 g of 2-bromo-6-methanesulfonylindan-1-one are dissolved in 15 ml of acetone and treated with stirring with 1.25 g of N,N'-diphenylthiourea in 25 ml of acetone. The hydrobromide of 5-methanesulfonyl-3-phenyl-2-phenylimino-2,3,8,8a-tetrahydro-indeno[1,2-d]thiazol-3a-ol crystallizes out of the clear solution after about 2 hours. After standing overnight, it is filtered off with suction and washed with a little acetone. 1.7 g of hydrobromide (m.p. 247° C.) are dissolved in 10 ml of methanol and treated with 0.8 ml of triethylamine. After 15 min, 150 ml of water are added and the mixture is stirred for 30 min with ice-cooling. The product formed is filtered off with suction and washed with a little cold water. 5-Methanesulfonyl-3-phenyl-2-phenylimino-2,3,8,8a-tetrahydroindeno[1,2-d]thiazol-3a-ol of melting point 172° C. is obtained. treated The hydrobromide of 5-methanesulfonyl-3-phenyl-2-phenylimino-2,3,8,8a-tetrahydro-indeno[1,2-d]thiazol-3a-ol crystallizes out of the clear solution after about 2 hours it is filtered off with suction washed with a little acetone 1.7 g of hydrobromide (m.p. 247° C.) are dissolved in 10 ml of methanol treated with 0.8 ml of triethylamine After 15 min 150 ml of water are added cooling The product formed is filtered off with suction washed with a little cold water

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

Procedure: Air is used as the oxygen-containing gas in the following example. 0.1 mol of diphenylthiourea, 1.2 mol of ammonia, and 0.02 mmol of Cu(OAc)2 are reacted with air (pressure of 5 bar) in a solvent mixture of 40 g of water and 40 g of methanol. Diphenylguanidine is obtained in a 94.2% yield at a reaction temperature of 50° C. and a reaction time of 70 min. containing gas in the following example

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

Procedure: 0.2 mol of diphenylthiourea, 75 g of methanol, 75 g of water, and 2.6 mol of ammonia are reacted at 50° C. with oxygen (1.5 bar), during which different amounts of Cu(OAc)2 are employed. The other experimental conditions and diphenyl-guanidine yields are listed in Table 5.

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

Procedure: The amount of ammonia is varied in the following examples. 0.2 mol of diphenylthiourea and ammonia together with 75 g of water, 75 g of methanol, and 0.1 mmol of Cu(OAc)2 are reacted with oxygen (1.5 bar). The other experimental conditions and diphenylguanidine yields are shown in Table 3.

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

Procedure: 1,3-Diphenylthiourea (114 mg, 0,5 mmol) was reacted with bis-(p-methoxyphenyl)-telluroxide for 16 h (methanol as solvent), the methanol was evaporated off under vacuum, the residue triturated with benzene and filtered to afford 1,3-diphenylurea as a white solid (72 mg, 68%), m.p. 234° (lit., 238°-239°). the methanol was evaporated off under vacuum the residue triturated with benzene filtered