ChemicalBook CAS DataBase List N-(3-NITROPHENYL)-N''-PHENYLUREA

N-(3-NITROPHENYL)-N''-PHENYLUREA synthesis

11synthesis methods

Product Name:N-(3-NITROPHENYL)-N''-PHENYLUREA
CAS Number:2000-54-6
Molecular formula:C13H11N3O3
Molecular Weight:257.24

3320-87-4
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62-53-3 Synthesis

62-53-3
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2000-54-6
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$106.00/50mg

Yield:2000-54-6 95%

Reaction Conditions:

in dichloromethane at 20; for 24 h;

Steps:

1-(3-Aminophenyl)-3-phenylurea, 2

Aniline (1.22ml, 13.4 mmol, 1.1 equiv) was added to a solution of 3-nitrophenyl isocyanate (2g, 12.2 mmol, 1 equiv) in dichloromethane (134 ml) and the reaction mixture was stirred overnight at room temperature. After stirring the mixture for 24 hours, upon solvent evaporation under reduced pressure, a white solid was obtained. Any excess aniline was washed from the solid with 1M HCl (2×50 ml) and the aqueous phase was extracted with ethyl acetate (2×50 ml). The organic phase was dried (MgSO₄) and concentrated under reduced pressure to yield the purified product, 1-(3-nitrophenyl)-3-phenylurea as a white solid (3.12g, yield 95%, Rf 0.57 (50% EtOAc in petroleum ether)). The product (2.9g, 11.3 mmol) and Pd/C (10%, 600 mg, 5.64 mmol, 0.5 equiv) were suspended in methanol (100 ml) and the reaction mixture was stirred overnight at room temperature under a hydrogen atmosphere. After removal of Pd/C by filtration through Celite the solvent was evaporated under reduced pressure. The title compound was thus obtained as a white solid (1.16 g, 33%). M.p.= 143-145 °C;ν_maxcm^-1:3296, 2182, 2033, 2005, 1962, 1649, 1594; δ_H(300 MHz, CD₃OD): 6.41 (1H, d, J= 8.0, Ar), 6.70 (1H, d, J= 8.0, Ar), 6.90 (1H, t, J= 2.0, Ar), 7.01 (2H, t, J= 8.0, Ar), 7.28 (2H, t, J= 8.0, Ar), 7.40 (2H, d, J= 8.0, Ar); δ_C(75 MHz, CD₃OD): 107.67, 110.61, 111.55, 120.33, 123.75, 129.81, 130.42, 140.42, 141.08, 149.04, 155.41; m/z (APCI) 228 ([M+H]⁺, 100%);found for ([M+H]⁺, 228.1132; C₁₃H₁₃ON₃+H⁺requires228.1131.

References:

Patil-Sen, Yogita;Dennison, Sarah R.;Snape, Timothy J. [Bioorganic and Medicinal Chemistry,2016,vol. 24,# 18,p. 4241 - 4245] Location in patent:supporting information