Ammonia → HCID 178481944, compound

HRID 1709318Notes

Reaction equation

HRID 1709318 reaction equation
[F:1][C:2]([F:10])([F:9])[C:3]([NH2:8])=[CH:4][C:5]([NH2:7])=[O:6].N.[CH3:12]NN.Cl>O.C(O)C>[CH3:12][N:8]1[C:3]([C:2]([F:10])([F:9])[F:1])=[CH:4][C:5]([OH:6])=[N:7]1

Participants

7

Reactant 4

HCID 222AmmoniaHCID 313Hydrochloric AcidHCID 6061MethylhydrazineHCID 86744155HCID 86744155, compound

Product 1

HCID 178481944HCID 178481944, compoundYield 65.3%

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 962WaterSolvent

Conditions

Temperature
30 °C

Procedure

30.82 g (0.2 mol) of 4,4,4-trifluoro-3-amino-2-butenamide (prepared by addition of 2 equivalents of ammonia to the corresponding alkenoic ester) was added to 10.1 g (0.22 mol) of methylhydrazine at room temperature. A slight exotherm raised the temperature to 30° C. The mixture was stirred for 1 hr. at which time the mixture became semi-solid; 10 ml. of ethanol was added to improve stirring. After another 1.5 hr., 7 ml. of ethanol was added, again to aid in stirring the mixture. After a total of 24 hr., the mixture was taken up in 25 ml. of water, the pH was adjusted to 6.5-7.0 with conc. hydrochloric acid (17 ml.), and the precipitated product was collected by filtration and dried to obtain 21.37 g (65.3%) of product m.p. 129°-131° C.

Workup

  1. stirringto improve stirring
  2. waitAfter another 1.5 hr
  3. stirringin stirring the mixture
  4. customAfter a total of 24 hr
  5. filtrationthe precipitated product was collected by filtration
  6. customdried

Sources & evidence

ORD record
ord-5687d6c5474d4121966c8d5b486f5bc7
Source dataset
uspto-grants-1990_08
Patent number
US04948902

Reaction notes

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