Phosgene → HCID 20406861, compound

HRID 615907Notes

Reaction equation

HRID 615907 reaction equation
[C:1]([O:5][CH3:6])(=[O:4])[NH:2][NH2:3].C(OCC)(=O)NN.[C:14](Cl)([Cl:16])=[O:15]>C(OCC)(=O)C>[CH3:6][O:5][C:1]([NH:2][NH:3][C:14]([Cl:16])=[O:15])=[O:4]

Participants

5

Reactant 3

HCID 6371PhosgeneHCID 20064Hydrazinecarboxylic acid, ethyl esterHCID 80519Methyl carbazate

Product 1

HCID 20406861HCID 20406861, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Example 1 was repeated but substituting methyl carbazate (50 g, 0.55 mole) for the ethyl carbazate and using phosgene (75 ml, 1.13 mole) in dry ethyl acetate as solvent. Solvent was removed under reduced pressure at a bath temperature <60° C. and the product was re-dissolved in ethyl acetate, filtered to remove insoluble material and recovered by evaporation of the solvent in vacuo, giving 2-methoxycarbonylhydrazinecarbonyl chloride (77 g, 92%) mp 55°-58° C. The ir spectrum was similar to that of 2-ethoxycarbonylhydrazinecarbonyl chloride.

Workup

  1. customSolvent was removed under reduced pressure at a bath temperature <60° C.
  2. dissolutionthe product was re-dissolved in ethyl acetate
  3. filtrationfiltered
  4. customto remove insoluble material
  5. customrecovered by evaporation of the solvent in vacuo

Sources & evidence

ORD record
ord-7fbf9c4140b6481f8584e6b20dc4a023
Source dataset
uspto-grants-1985_02
Patent number
US04501860

Reaction notes

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