Reaction #657298

ord-79a1adf6b66d43e1883b3118f90eaa55

Reaction equation

O=C([O-])[O-].[K+].[K+]
Potassium carbonate
O=C(O)CCl
Monochloroacetic acid
O=C([O-])[O-].[K+].[K+]
potassium carbonate
O=C=O
CO2
NN.O
hydrazine hydrate
→
NN(CC(=O)O)CC(=O)O
2,2′-(hydrazine-1,1-diyl)diacetic acid

Reactants

O=C([O-])[O-].[K+].[K+]
Potassium carbonate
O=C(O)CCl
Monochloroacetic acid
O=C([O-])[O-].[K+].[K+]
potassium carbonate
O=C=O
CO2
NN.O
hydrazine hydrate

Reagents

None

Solvents

O
water

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    Otherrose to 70° C
  2. 2
    TemperatureThe solution was then heated until the gas evolution
  3. 3
    OtherAt the end of the reaction
  4. 4
    Otherthe 2,2′-(hydrazine-1,1-diyl)diacetic acid was precipitated
  5. 5
    OtherThe product (mp 171° C.) was crystallized from water

Procedure

Monochloroacetic acid (2 eq.) in water was neutralized with potassium carbonate (1 eq.) followed by the addition of hydrazine hydrate (1 eq.). Potassium carbonate (1 eq.) was added to the solution gradually, whereupon, with a steady evolution of CO2, the temperature rose to 70° C. The solution was then heated until the gas evolution stopped. At the end of the reaction, the 2,2′-(hydrazine-1,1-diyl)diacetic acid was precipitated by making the solution acidic with concentrated HCl. The product (mp 171° C.) was crystallized from water, and was confirmed by NMR spectroscopy and elemental analysis.

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US09023837B2uspto-grants-2015_05