1,3-diphenylurea

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:120.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: In a capped vial (1 mL) containing a solution of phenylazide (6.6 mg, 55 μmol) in dry THF (300 μL), was added [RhCl(cod)]2 (0.27 mg, 0.55 μmol), and 1,2-bis(diphenylphosphino)ethane (0.44 mg, 1.1 μmol) and was shaken until the solution was homogeneous. After addition of aniline (10 μL, 110 μmol), the resulting mixture was transferred to the micro-autoclave, which was pre-charged with [11C]CO. The autoclave (250 μL) was heated at 120° C. for 5 min under 35 MPa and the crude product was transferred to a reduced pressure vial. The radioactivity was measured before and after the vial was flushed with N2 (the [11C]CO-trapping efficiency of 82% was determined based on these values). A small amount of crude product was collected and analyzed by the reversed phase HPLC. Yield of product: 82%. The product was identified by HPLC with an added authentic reference compound. was pre-charged with [11C]CO was flushed with N2 (the [11C]CO- A small amount of crude product was collected

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

Procedure: In a most preferred embodiment of the process of this invention, a solution of 0.05 equivalents of the isatin derivative, 0.06 mole equivalents of the carbanilide, and 0.30 moles of aluminum chloride in 200 ml. of nitrobenzene are maintained at 100° C for about 12 hours. The cooled solution is poured into one liter of ice water and 600 ml. of hexane to precipitate the product. After filtering, the product is suspended in 200 ml. of acetic acid, 5 ml. of water, and 20 ml. of sulfuric acid. This solution is refluxed for approximately 24 hours, cooled and filtered. This refluxing hydrolyzes the reacted anilide and yields the desired oxindole diamine derivative. The filtrate containing the oxindole diamine derivative is neutralized with sodium carbonate and the solution concentrated in vacuo and taken in about 300 ml. of boiling 1N hydrochloric acid. This solution is diluted in about 300 ml. of water, cooled to about 5° C, filtered, and made basic with ammonia to precipitate the product. The product is collected and may be recrystallized from a dioxane hexane solution to yield the pure oxindole diamine derivative. of hexane to precipitate the product After filtering This solution is refluxed for approximately 24 hours cooled filtered

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

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

Procedure: 1.19 g phenyl isocyanate and 0.6 g acetic acid were reacted in a 1:1 isocyanate:acetic acid molar ratio. The reaction, product isolation and analysis were conducted as in Example 1. 0.45 g diphenyl urea and 0.9 g acetanilide were obtained. The reaction, product isolation and analysis

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

Procedure: 1.19 g phenyl isocyanate and 0.6 g acetic acid were reacted in a 1:1 isocyanate:acetic acid molar ratio. The reaction, product isolation and analysis were conducted as in Example 1. 0.45 g diphenyl urea and 0.9 g acetanilide were obtained. The reaction, product isolation and analysis

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

Procedure: After 45 minutes at 160° C., the solution contained 0.050 mole each of methyl N-phenyl carbamate and aniline, representing quantitative urea alcoholysis.

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

Procedure: After 45 minutes at 160° C., the solution contained 0.050 mole each of methyl N-phenyl carbamate and aniline, representing quantitative urea alcoholysis.

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

Procedure: The above reaction was carried out in a high-grade stainless steel autoclave fitted with a polytetrafluoroethylene beaker of 100 cm3 capacity. 0.0373 g (0.1 mmole) of N,N′-bis(salicylidene)-1,2-phenylenediaminocobalt(II), 0.0172 g (0.1 mmole( of p-toluenesulfonic acid, 4.6498 g (50.0 mmole) aniline, 1.2318 g (10.0 mmole) of nitrobenzene and 8.69 g (10 mmole) of toluene were mixed in the autoclave. The autoclave was flushed three times with gaseous nitrogen and then was pressurized with 50 bar carbon monoxide. After the gas supply was interrupted, the autoclave was inserted into an aluminum block that had been preheated to 200° C. Following 5 minutes, the autoclave reaction temperature reached 170° C. which thereupon was kept constant. Following 6 h of reaction, the autoclave was cooled with cold water and ice and reached room temperature in 5 minutes. The reaction mixture was filtered off and the solid substance so obtained was washed with toluene (3×10 ml). Thereupon the solid substance was dried in high vacuum for 4 h. Characterization was implemented by 1H-NMR, MS, CHN analysis and melting point. This test, not yet optimized, gave 3.0414 g of N,N′-diphenylurea, relating to a yield of 23.9%. The above reaction The autoclave was flushed three times with gaseous nitrogen had been preheated to 200° C reached 170° C. Following 6 h of reaction reached room temperature in 5 minutes The reaction mixture was filtered off the solid substance so obtained was washed with toluene (3×10 ml) Thereupon the solid substance was dried in high vacuum for 4 h