N'-hydroxy-4-iodobenzenecarboximidamide

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:; See reaction.notes.procedure_details.

Procedure: To a suspension of the product obtained in Step A above (8.43 g, 32.17 mmol) in 200 ml of CH2Cl2 there are added 6.72 ml (48.2 mmol) of triethylamine. 3.34 ml (35.4 mmol) of acetic anhydride are added dropwise and the solution is stirred overnight at ambient temperature. After washing 3 times with water and then with brine, the organic phase is dried over MgSO4 and evaporated. The solid obtained is taken up in isopropyl ether and then filtered to yield the title product. After washing 3 times with water with brine, the organic phase is dried over MgSO4 evaporated The solid obtained filtered

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

Procedure: To a suspension of the product obtained in Step A above (8.43 g, 32.17 mmol) in 200 ml of CH2Cl2 there are added 6.72 ml (48.2 mmol) of triethylamine. 3.34 ml (35.4 mmol) of acetic anhydride are added dropwise and the solution is stirred overnight at ambient temperature. After washing 3 times with water and then with brine, the organic phase is dried over MgSO4 and evaporated. The solid obtained is taken up in isopropyl ether and then filtered to yield the title product. After washing 3 times with water with brine, the organic phase is dried over MgSO4 evaporated The solid obtained filtered

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

Procedure: 17.3 g (249 mmol) of hydroxylamine hydrochloride and then 35 ml (251 mmol) of triethylamine are added to 80 ml of DMSO. A voluminous white precipitate forms, and the reaction mixture is diluted with a small amount of THF. After stirring for 1 hour, the precipitate is filtered off. The filtrate is collected and then transferred to a flask to which there are added 9.55 g (41.7 mmol) of 4-iodobenzonitrile. The reaction mixture is stirred overnight at ambient temperature and is then cooled in an ice bath and 200 mL of water are added. The precipitate is filtered off to yield the expected product. the precipitate is filtered off The filtrate is collected transferred to a flask to which there The reaction mixture is stirred overnight at ambient temperature is then cooled in an ice bath The precipitate is filtered off

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

Procedure: A mixture of 4-iodobenzamidoxime (3.93 g) in triethylorthoformate (15 ml) was heated at reflux for 4 hours. The mixture was evaporated and the residue was purified by flash column chromatography on silica gel using 4:1 (v/v) n-pentane/ethyl acetate as eluent to give 3-(4-iodophenyl)-1,2,4-oxadiazole (0.74 g) as a solid; NMR(CDCl3): 7.85(4H,s) and 8.74(1H,s); m/z 272(M). was heated at reflux for 4 hours The mixture was evaporated the residue was purified by flash column chromatography on silica gel using 4:1 (v/v) n-pentane/ethyl acetate as eluent

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

Procedure: A mixture of 4-iodobenzamidoxime (3.93 g) in triethylorthoformate (15 ml) was heated at reflux for 4 hours. The mixture was evaporated and the residue was purified by flash column chromatography on silica gel using 4:1 (v/v) n-pentane/ethyl acetate as eluent to give 3-(4-iodophenyl)-1,2,4-oxadiazole (0.74 g) as a solid; NMR(CDCl3): 7.85(4H,s) and 8.74(1H,s); m/z 272(M). was heated at reflux for 4 hours The mixture was evaporated the residue was purified by flash column chromatography on silica gel using 4:1 (v/v) n-pentane/ethyl acetate as eluent

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

Procedure: Acetyl chloride (1.62 ml) was added to a solution of 4-iodobenzamidoxime (5.24 g) in pyridine (35 ml) at ambient temperature. The reaction mixture was heated at reflux for 3 hours. The mixture was cooled to ambient temperature, evaporated and ice-water was added to the residue. The solid was collected by filtration, washed with water and recrystallised from acetonitrile to give 3-(4-iodophenyl)-5-methyl-1,2,4-oxadiazole (4.43 g), m.p. 121°-122° C.; microanalysis found: C, 37.6; H, 2.4; N, 9.7%; C9H7IN2O requires: C, 37.8; H, 2.47; N, 9.79%; NMR: 2.66(3H,s), 7.77(2H,dd) and 7.94(2H,dd); m/z 287(M+H). The reaction mixture was heated at reflux for 3 hours evaporated ice-water was added to the residue The solid was collected by filtration washed with water recrystallised from acetonitrile

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

Procedure: A mixture of 4-iodobenzonitrile (7.69 g), anhydrous sodium carbonate (6.25 g), hydroxylamine hydrochloride (8.74 g), in water (60 ml) and sufficient ethanol to maintain a clear solution, was heated at 90°-100° C. for 4 hours. The reaction mixture was cooled to ambient temperature and evaporated until a precipitate formed. The solid was collected by filtration, washed with water and recrystallised from acetonitrile to give 4-iodobenzamidoxime (5.97 g), m.p. 155°-161° C.; microanalysis, found: C, 31.4; H, 2.7; N, 10.2%; C7H7IN2 O 0.2H2O requires: C, 31.6; H, 2.81; R, 10.5%; NMR: 5.82(2H,s), 7.46(2H,d), 7.73(2H,d), 9.69(1H,s); m/z 263(M+H). was heated at 90°-100° C. for 4 hours evaporated until a precipitate formed The solid was collected by filtration washed with water recrystallised from acetonitrile

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

Procedure: A mixture of 4-iodobenzonitrile (7.69 g), anhydrous sodium carbonate (6.25 g), hydroxylamine hydrochloride (8.74 g), in water (60 ml) and sufficient ethanol to maintain a clear solution, was heated at 90°-100° C. for 4 hours. The reaction mixture was cooled to ambient temperature and evaporated until a precipitate formed. The solid was collected by filtration, washed with water and recrystallised from acetonitrile to give 4-iodobenzamidoxime (5.97 g), m.p. 155°-161° C.; microanalysis, found: C, 31.4; H, 2.7; N, 10.2%; C7H7IN2 O 0.2H2O requires: C, 31.6; H, 2.81; R, 10.5%; NMR: 5.82(2H,s), 7.46(2H,d), 7.73(2H,d), 9.69(1H,s); m/z 263(M+H). was heated at 90°-100° C. for 4 hours evaporated until a precipitate formed The solid was collected by filtration washed with water recrystallised from acetonitrile

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