Triethylamine → HCID 13788330, compound

HRID 1437277Notes

Reaction equation

HRID 1437277 reaction equation
C(N(CC)CC)C.Cl[C:9]([O:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[O:10].[C:19]([O:23][CH2:24][CH3:25])(=[O:22])[NH:20][NH2:21]>C(Cl)Cl>[NH:21]([C:9]([O:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[O:10])[NH:20][C:19]([O:23][CH2:24][CH3:25])=[O:22]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 10387Benzyl chloroformateHCID 20064Hydrazinecarboxylic acid, ethyl ester

Product 1

HCID 13788330HCID 13788330, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Triethylamine (100 mL) and benzyl chloroformate (103 mL) were added to ethyl carbazate (50.0 g) in methylene chloride (400 mL) at 0° C., followed by stirring at room temperature for 18 hours. The reaction mixture was partitioned by use of saturated aqueous sodium hydrogencarbonate and chloroform. The organic layer was washed with brine, and then dried over magnesium sulfate anhydrate, followed by filtration. The solvent was removed under reduced pressure, and the residue was purified through silica gel column chromatography (hexane-ethyl acetate), to thereby give benzyl ethyl hydrazine-1,2-dicarboxylate as an oily product (31.7 g, 27.7%).

Workup

  1. customThe reaction mixture was partitioned by use of saturated aqueous sodium hydrogencarbonate and chloroform
  2. washThe organic layer was washed with brine
  3. dry with materialdried over magnesium sulfate anhydrate
  4. filtrationfollowed by filtration
  5. customThe solvent was removed under reduced pressure
  6. customthe residue was purified through silica gel column chromatography (hexane-ethyl acetate)

Sources & evidence

ORD record
ord-45b9131d51954368bb35b9ce3c091ec6
Source dataset
uspto-grants-2009_11
Patent number
US07622471B2

Reaction notes

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