Hydrochloric Acid → HCID 13305521, compound

HRID 1578202Notes

Reaction equation

HRID 1578202 reaction equation
C(Cl)(Cl)=O.ON=C(C(OCC)=O)C(OCC)=O.CN(C)C1C=CC=CC=1.[CH3:27][O:28][C:29]1[CH:36]=[CH:35][C:32]([CH2:33][OH:34])=[CH:31][CH:30]=1.Cl[C:38]([O:40][N:41]=[C:42]([C:48]([O:50][CH2:51][CH3:52])=[O:49])[C:43]([O:45][CH2:46][CH3:47])=[O:44])=[O:39].Cl>C1C=CC=CC=1.O.N1C=CC=CC=1>[CH3:27][O:28][C:29]1[CH:36]=[CH:35][C:32]([CH2:33][O:34][C:38]([O:40][N:41]=[C:42]([C:48]([O:50][CH2:51][CH3:52])=[O:49])[C:43]([O:45][CH2:46][CH3:47])=[O:44])=[O:39])=[CH:31][CH:30]=1

Participants

10

Reactant 6

HCID 313Hydrochloric AcidHCID 949N,N-DimethylanilineHCID 6371PhosgeneHCID 77384-Methoxybenzyl alcoholHCID 6399380Diethyl (hydroxyimino)malonateHCID 20567984Diethyl 2-chlorocarbonyloxyiminomalonate

Product 1

HCID 13305521HCID 13305521, compound

Reagents, catalysts & solvents 3

HCID 241BenzeneSolvent4×HCID 962WaterSolventHCID 1049PyridineSolvent

Procedure

Benzene (20 ml.) was added to a solution of phosgene 2.5 g.) in benzene (11.4 ml.). A solution of diethyl 2-hydroxyiminomalonate (4.73 g.) and N,N-dimethylaniline (3.03 g.) in benzene (30 ml.) was added dropwise to the solution over 40 minutes at 5° C. in a nitrogen stream. The mixture was stirred for 1 hour at the same temperature and overnight at room temperature. A solution of 4-methoxybenzylalcohol (3.11 g.) and pyridine (4.04 ml.) in benzene (30 ml.) was added dropwise the the resultant mixture containing diethyl 2-chlorocarbonyloxyiminomalonate over a period of 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 1 N-hydrochloric acid (20 ml.) was added thereto, after which the mixture was shaken. The organic layer was then washed 3 times with 1 N 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.), a pale brown oil, which was solidified on standing at ambient temperature.

Workup

  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. washThe organic layer was then washed 3 times with 1 N 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
  9. distillationthe solvent was distilled off

Sources & evidence

ORD record
ord-cd0c9a15597a4c02a180261074c7f71c
Source dataset
uspto-grants-1981_09
Patent number
USRE030752

Reaction notes

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