Hydrochloric Acid → HCID 178481949, compound

HRID 358334Notes

Reaction equation

HRID 358334 reaction equation
C[O:2][C:3](=O)[C:4]([Cl:8])=[C:5](Cl)[Cl:6].[CH3:10][NH:11][NH2:12].C(=O)([O-])[O-].[K+].[K+].Cl>C1(C)C=CC=CC=1>[Cl:8][C:4]1[C:3]([OH:2])=[N:12][N:11]([CH3:10])[C:5]=1[Cl:6]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6061Methylhydrazine2×HCID 11430Potassium CarbonateHCID 525088Methyl trichloropropenoate

Product 1

HCID 178481949HCID 178481949, compoundYield 93.3%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 74 gms (0.391 mol) methyl-2,3,3-trichloroacrylate, 18 gms (21 ml) methyl hydrazine and 54 gms (0.391 mol) potassium carbonate in 500 ml toluene was stirred at room temperature for one day, and then heated to reflux for one day. An additional 5 gms methyl hydrazine was then added and the reaction mixture was stirred an additional day at reflux. The reaction mixture was then acidified with dilute hydrochloric acid. At this point, there was a large amount of solid which did not dissolve in either phase. The solids were removed by filtration, resuspended in water and the suspension was filtered again. The solids were air-dried overnight, yielding 60.9 gms of product, melting point 212°-216° C.

Workup

  1. temperatureheated
  2. temperatureto reflux for one day
  3. stirringthe reaction mixture was stirred an additional day
  4. temperatureat reflux
  5. dissolutiondid not dissolve in either phase
  6. customThe solids were removed by filtration
  7. filtrationthe suspension was filtered again
  8. customThe solids were air-dried overnight

Sources & evidence

ORD record
ord-37926b42fc5448cb8863973e4bd1e392
Source dataset
uspto-grants-1984_08
Patent number
US04466962

Reaction notes

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