Hydrochloric Acid → HCID 13305521, compound

Benzene (20 ml.) was added to a solution of phosgene 2.5 g.) in benzene (11.4 ml.). To the solution was dropwise added a solution of diethyl 2-hydroxyiminomalonate (4.73 g.) and N,N-dimethylaniline (3.03 g.) in benzene (30 ml.) over 40 minutes at 5° C in nitrogen stream. The mixture was stirred for 1 hour at the same temperature and overnight at room temperature. To the resultant mixture containing diethyl 2-chlorocarbonyloxyiminomalonate was dropwise added a solution of 4-methoxybenzyl alcohol (3.11 g.) and pyridine (4.04 ml.) in benzene (30 ml.) over 40 minutes at 5° C. The mixture was stirred for 2 hours at the same temperature, for 3 hours at room temperature and allowed to stand overnight. Cold water (100 ml.) was added to the reaction mixture to dissolve an insoluble material and cooled 1N-hydrochloric acid (20 ml.) was added thereto, after which the mixture was shaken. The organic layer was in turn washed 3 times with 1N hydrochloric acid (20 ml.), 3 times with a 5% sodium carbonate aqueous solution (20 ml.) and a sodium chloride aqueous solution, and then dried over magnesium sulfate. After drying the solvent was distilled off to give diethyl 2-(4-methoxybenzyloxycarbonyloxyimino)malonate (6.89 g.), pale brown oil, which was solidified on standing at ambient temperature.

1. stirringThe mixture was stirred for 2 hours at the same temperature, for 3 hours at room temperature
2. waitto stand overnight
3. dissolutionto dissolve an insoluble material
4. additionwas added
5. stirringafter which the mixture was shaken
6. washwashed 3 times with 1N hydrochloric acid (20 ml.), 3 times with a 5% sodium carbonate aqueous solution (20 ml.)
7. dry with materiala sodium chloride aqueous solution, and then dried over magnesium sulfate
8. customAfter drying the solvent
9. distillationwas distilled off

ORD record

ord-f604fad4f5064d76bdc0b29f6e024f3f

Source dataset

uspto-grants-1977_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04010178