Hydrochloric Acid → HCID 67158418, compound

Temperature

100 °C

11.0 g (48.0 mmol) of 3-amino-2-methyl-4-methylsulfonylbenzoic acid (synthesis described by T. L. Siddall et al. in Pest Management Science (2002), 58 (12), 1175-1186) was added to a solution of 2.03 g (50.9 mmol) of NaOH in 60 ml of water. 3.31 g (48.0 mmol) of sodium nitrite were then added. At 5-8° C., the solution was added dropwise to a mixture of concentrated HCl and ice. The mixture was stirred at this temperature for 15 minutes and then neutralized with sodium acetate. The content was then added dropwise to a solution, kept at 70-80° C., of 21.54 g (134.3 mmol) of potassium ethyl xanthogenate in 80 ml of water. The mixture was stirred at 80° C. for 15 minutes and then, at RT, acidified for work-up with 1M HCl. After five minutes, the mixture was decanted and 85 ml of 10% strength aqueous sodium hydroxide solution were added to the residue. The mixture was heated and distillate formed was removed with the aid of a distillation assembly, so that an internal temperature of 100° C. could be reached. After the mixture had been heated at this temperature for 1.25 h, HPLC analysis showed that the reaction had gone to completion. 21 ml of a saturated aqueous sodium bisulfite solution were then added, and the mixture was heated at 100° C. for 10 minutes. For work-up, the cooled reaction mixture was acidified with 1M HCl, cooled to 0-5° C. and filtered under an atmosphere of nitrogen. What was isolated were 10 g of a solid; a 1H-NMR spectrum showed the identity of the product.

1. additionThe content was then added dropwise to a solution
2. stirringThe mixture was stirred at 80° C. for 15 minutes
3. customat RT
4. waitAfter five minutes
5. customthe mixture was decanted
6. addition85 ml of 10% strength aqueous sodium hydroxide solution were added to the residue
7. temperatureThe mixture was heated
8. customdistillate formed
9. customwas removed with the aid of a distillation assembly
10. customso that an internal temperature of 100° C.
11. temperatureAfter the mixture had been heated at this temperature for 1.25 h
12. addition21 ml of a saturated aqueous sodium bisulfite solution were then added
13. customFor work-up, the cooled reaction mixture
14. temperaturecooled to 0-5° C.
15. filtrationfiltered under an atmosphere of nitrogen
16. customWhat was isolated

ORD record

ord-b4cab5ef1a61405ea01107843db9ee0c

Source dataset

uspto-grants-2011_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07943551B2