Ammonium Chloride → HCID 20456205, compound

Temperature

0 °C

0.1 g of sodium was dissolved in 10 ml of methanol, under nitrogen. 1.5 g of 3A was stirred in 12 ml of dry methanol at 0° C. under nitrogen and 0.23 ml of the sodium methoxide solution was added drop-by-drop at 0° C. The resulting mixture was stirred at 0° C. for 3.5 hours, then stored in a freezer over a week-end. Then 30 mg of ammonium chloride was added, the mixture was stirred for 15 minutes at 0° C., stripped to a mush, slurried with ether and filtered. The ether was evaporated from the filtrate, the residue was dissolved in 25 ml of tetrahydrofuran and the solution was added drop-by-drop over one minute to a vigorously stirred ice-cold 0.2N hydrochloric acid solution. The resulting mixture was stirred at 0° C. for 3.5 hours, the solvent was evaporated and the residue was extracted with ether. The water was evaporated from the aqueous phase, toluene was added to the residue and residual water removed by azeotropic distillation. The residue was dissolved in methanol, toluene was added and the mixture was distilled azeotropically. The residue was dissolved in methylene chloride, the solution was dried (Na2SO4), filtered and the solvent was evaporated. The residue was subjected to low pressure distillation, to give 3, as a gum.

1. waitstored in a freezer over a week
2. stirringthe mixture was stirred for 15 minutes at 0° C.
3. filtrationfiltered
4. customThe ether was evaporated from the filtrate
5. dissolutionthe residue was dissolved in 25 ml of tetrahydrofuran
6. additionthe solution was added drop-by-drop over one minute to a vigorously stirred ice-cold 0.2N hydrochloric acid solution
7. stirringThe resulting mixture was stirred at 0° C. for 3.5 hours
8. customthe solvent was evaporated
9. extractionthe residue was extracted with ether
10. customThe water was evaporated from the aqueous phase, toluene
11. additionwas added to the residue and residual water
12. customremoved by azeotropic distillation
13. dissolutionThe residue was dissolved in methanol
14. additiontoluene was added
15. distillationthe mixture was distilled azeotropically
16. dissolutionThe residue was dissolved in methylene chloride
17. dry with materialthe solution was dried (Na2SO4)
18. filtrationfiltered
19. customthe solvent was evaporated
20. distillationThe residue was subjected to low pressure distillation
21. customto give 3

ORD record

ord-4f87d43bfdb24cdca13976f3c6586df0

Source dataset

uspto-grants-1986_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04582529