4-(4-Chlorophenoxy)benzenamine

General procedure: A mixture of 1-substituted-4-nitrobenzene (9.3mmol) and N2H4*H2O (27.9 mmol) in 20 ml ethanol was stirred for 10 min at 28-30 °C. The suspension of Raney-Ni in water (0.02 g, 4.41 ml) was added by stirring in three portions at 10 minute intervals. After 30 min, when reaction had subsided, stirring was continued for further 6 h at 50-60 °C. The catalyst was removed by filtration. The solvent was evaporated to obtain compounds 6-10:B. 4-(4-Chloro-phenoxy)-shenylisothiocvanate. To a solution of 1, 1'- thiocarbonyldiimidazole (4.99 g, 28 mmol) in CH2CI2 (100 mL) was added a solution of 4- (4-chloro-phenoxy)-phenylamine (2.19 g, 10 mmol) in CH2CI2 (100 mL) dropwise over 1 h at 0 °C. The ice bath was removed, and the reaction mixture was stirred for 30 min at rt. The mixture was then washed with NaHCO3 (50 mL) and brine (50 mL). The organics were dried (Na2SO4), concentrated, passed through a plug of silica gel, and then washed with 20percent EtOAc/hexanes to afford 2.6 g (99percent) of the desired product NMR (400 MHz, CDC13) : 7.25-7. 23 (m, 2H), 7.13-7. 10 (m, 2H), 6.89-6. 84 (m, 4H).EXAMPLE 3 (S)-2- {3- [4- (4-Chloro-phenoxy)-phenyl]-ureido}-N (2-diisopropylamino-ethyl)-3- phenyl-propionamide. A. f4- (4-Chloro-phenoxy)-phenvll-carbamic acid phenyl ester. To a solution of 4- (4-chloro-phenoxy)-phenylamine (2.2 g, 10 mmol) in THF (30 mL) at 0 °C, was added pyridine (0.98 g, 12.5 mmol) followed by phenylchloroformate (1.61 g, 10.3 mmol). After the mixture was stirred for 10 min, the ice bath was removed. After further stirring for 2.5 h at rt, the mixture was diluted with EtOAc (150 mL) and washed sequentially with 10percent HCI (40 mL), H20 (40 mL), saturated NaHCO3 (40 mL) and brine (40 mL). The organics were dried (Na2SO4), and the solvents were removed. The residue was recrystallized from CH2CI2/hexanes to afford 2.8 g (85percent) of the desired product. MS (electrospray) : mass calculated for C19H, 4CINO3, 339.07 ; m/z found, 340.0 [M+H] +, 362.0 [M+Na] +.'H NMR (400 MHz, DMSO-d6) : 10. 32 (br s, 1 H), 7.57- 6.96 (m, 13H).

Molecular Weight:219.66
XLogP3:2.7
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:2
Exact Mass:219.0450916
Monoisotopic Mass:219.0450916
Topological Polar Surface Area:35.2
Heavy Atom Count:15
Complexity:184
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes