Urea → 1,2,3-trichloro-5-iodobenzene

Temperature

80 °C

Into a suspension of 25.0 g of 3,4,5-trichloroaniline in 10 mL of acetonitrile, 25 mL of methanol and 100 mL of water, a solution of 9.7 g of sodium nitrite in 25 mL of water was dropped while stirring and ice-cooling the suspension over 20 minutes and after the completion of the dropping, the resultant mixture was stirred at 5 to 6° C. for 30 minutes. Next, the reaction mixture was dropped into 75 mL of an aqueous solution of 23.2 g of potassium iodide which was heated to 80° C. over 20 minutes and after the completion of the dropping, the resultant mixture was continuously stirred at the same temperature further for 1 hour. After the completion of the reaction, 50 mL of an aqueous solution of 7.64 g of urea was added to the reaction mixture and the resultant mixture was left to be cooled down to room temperature while stirring the mixture, followed by diluting the mixture with 400 mL of ethyl acetate. Subsequently, an insoluble substance was filtered off from the mixture by Celite filtration. The organic phase was washed with 300 mL of a saturated sodium hydrogen sulfite aqueous solution and next with 200 mL of water and then dehydrated and dried over saturated saline and anhydrous sodium sulfate in this order, and the solvent was distilled off under reduced pressure. The resultant residue was purified by silica gel column chromatography eluting with hexane to obtain 29.3 g of the objective substance as a light yellow crystal.

1. temperatureice-cooling the suspension over 20 minutes
2. additionwas added to the reaction mixture
3. temperatureto be cooled down to room temperature
4. stirringwhile stirring the mixture
5. filtrationSubsequently, an insoluble substance was filtered off from the mixture by Celite filtration
6. washThe organic phase was washed with 300 mL of a saturated sodium hydrogen sulfite aqueous solution and next with 200 mL of water
7. dry with materialdried over saturated saline and anhydrous sodium sulfate in this order
8. distillationthe solvent was distilled off under reduced pressure
9. customThe resultant residue was purified by silica gel column chromatography
10. washeluting with hexane
11. customto obtain 29.3 g of the objective substance as a light yellow crystal

ORD record

ord-98b6338d16a64f20b200bf57412ce66c

Source dataset

uspto-grants-2012_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08318757B2