Hydrochloric Acid → HCID 12595487, compound

Temperature

80 °C

3N hydrochloric acid (300 milliliters) was added to 2,5-diphenylanilin obtained in the foregoing (25 g, 101.91 mmol, 1.0 equivalent), and the mixture was stirred at 80° C. for 2.5 hours. After that, the mixture was cooled to room temperature. After that, the mixture was further cooled to 5° C. While the temperature of the mixture was kept at 10° C. or lower (5 to 8° C.), an aqueous solution of sodium nitrite (NaNO2: 8.43 g, 122.29 mmol, 1.2 equivalents, H2O: 60 milliliters) was slowly added to the mixture, and the whole was stirred for 0.5 hour. The reaction liquid was dropped into an aqueous solution of potassium iodide (KI: 60.9 g, 366.87 mmol, 3.6 equivalents, H2O: 180 milliliters). An appropriate amount of methylene chloride was further added to the mixture so that a reaction was completed, and the whole was stirred for 0.75 hour at room temperature. Sodium hydrogen dithionite was added to the reaction liquid until the color of the reaction liquid was turned into a yellow color. After that, the mixture was stirred for 0.5 hour, and the organic layer of the resultant reaction liquid was extracted. The extracted organic layer was washed with a saturated salt solution, dried with anhydrous sodium sulfate, and concentrated. The resultant residue was purified by short column chromatography (methylene chloride) and silica gel chromatography (methylene chloride:hexane=1:1→2:1), and the purified residue was dried, whereby a pale pink solid was obtained (24.35 g, yield: 67%).

1. customobtained in the foregoing (25 g, 101.91 mmol, 1.0 equivalent)
2. temperatureAfter that, the mixture was cooled to room temperature
3. temperatureAfter that, the mixture was further cooled to 5° C
4. customwas kept at 10° C.
5. stirringthe whole was stirred for 0.5 hour
6. customThe reaction liquid
7. stirringthe whole was stirred for 0.75 hour at room temperature
8. stirringAfter that, the mixture was stirred for 0.5 hour
9. customthe organic layer of the resultant reaction liquid
10. extractionwas extracted
11. washThe extracted organic layer was washed with a saturated salt solution
12. dry with materialdried with anhydrous sodium sulfate
13. concentrationconcentrated
14. customThe resultant residue was purified by short column chromatography (methylene chloride) and silica gel chromatography (methylene chloride:hexane=1:1→2:1)
15. customthe purified residue was dried
16. customwhereby a pale pink solid was obtained (24.35 g, yield: 67%)

ORD record

ord-f7713d90277c4658b7c6b088a0d569a4

Source dataset

uspto-grants-2013_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08586199B2