Hydrochloric Acid → HCID 22617105, compound

HRID 843294Notes

Reaction equation

HRID 843294 reaction equation
[C:1]([O:5][CH3:6])(=[O:4])[NH:2]N.Cl.[C:8](=[NH:23])([O:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[O:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1>O>[O:16]([C:8]([O:9][C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1)=[N:23][NH:2][C:1]([O:5][CH3:6])=[O:4])[C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 80519Methyl carbazateHCID 13676208HCID 13676208, compound2×

Product 1

HCID 22617105HCID 22617105, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

4.31 g (46.9 mmol) of methyl carbazate were initially charged in water (40 ml) and admixed with 4.75 g (46.9 mmol) of conc. hydrochloric acid (36% strength). 10.0 g (46.9 mmol) of diphenyl imidocarbonate (preparation of diphenyl imidocarbonate similar to the method of Heydayatullah, M. Bull Soc. Chim Fr. 1967, 416) were added a little at a time to this solution, at 7° C. After 4 hours of stirring with ice-bath cooling, the mixture was extracted with ethyl acetate (4×100 ml). The combined organic phases were dried over magnesium sulphate and, after filtration, concentrated under reduced pressure. The residue was dried under reduced pressure at 25° C. This gave 7.62 g of crude product containing phenol and methyl N′-diphenoxymethylenehydrazinecarboxylate in a ratio of 10:1. The yield of methyl N′-diphenoxymethylene-hydrazinecarboxylate was 693 mg (5%).

Workup

  1. addition1967, 416) were added a little at a time to this solution
  2. customat 7° C
  3. temperaturecooling
  4. extractionthe mixture was extracted with ethyl acetate (4×100 ml)
  5. dry with materialThe combined organic phases were dried over magnesium sulphate
  6. filtrationafter filtration
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was dried under reduced pressure at 25° C
  9. additionThis gave 7.62 g of crude product containing phenol and methyl N′-diphenoxymethylenehydrazinecarboxylate in a ratio of 10:1

Sources & evidence

ORD record
ord-2e09cec4a1a54c6eaddb6bc1bfe129f0
Source dataset
uspto-grants-2002_04
Patent number
US06376699B1

Reaction notes

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