Methylamine → HCID 85684080, compound

HRID 515872Notes

Reaction equation

HRID 515872 reaction equation
[F:1][C:2]([F:12])([F:11])[C:3](=O)[CH2:4][C:5]([O:7][CH2:8][CH3:9])=[O:6].[CH3:13][NH2:14].C(O[CH:19](Br)[CH2:20]Br)(=O)C>>[CH3:13][N:14]1[CH:20]=[CH:19][C:4]([C:5]([O:7][CH2:8][CH3:9])=[O:6])=[C:3]1[C:2]([F:12])([F:11])[F:1]

Participants

4

Reactant 3

HCID 6329MethylamineHCID 32381Ethanol, 1,2-dibromo-, 1-acetateHCID 67793Ethyl 4,4,4-trifluoroacetoacetate

Product 1

HCID 85684080HCID 85684080, compound

Conditions

Temperature
10 °C

Procedure

Ethyl 4,4,4-trifluoro-3-oxo-butanoate (29 ml, 0.219 mmol) is added to methylamine (40% solution in water) (50 ml, 0.580 mmol) cooled to 10° C.; a white precipitate forms. 1,2-Dibromoethyl acetate (prepared according to Molecules, 16, 9368-9385; 2011) is added dropwise. The reactor is then sealed and heated at 70° C. for 45 minutes. The reaction mixture is cooled, then extracted with ethyl acetate, dried over sodium sulphate (Na2SO4) and evaporated to dryness. The crude reaction product obtained is purified by chromatography over silica gel using heptane and ethyl acetate as eluants. The expected compound is obtained in the form of crystals.

Workup

  1. customThe reactor is then sealed
  2. temperatureheated at 70° C. for 45 minutes
  3. temperatureThe reaction mixture is cooled
  4. extractionextracted with ethyl acetate
  5. dry with materialdried over sodium sulphate (Na2SO4)
  6. customevaporated to dryness
  7. customThe crude reaction product
  8. customobtained
  9. customis purified by chromatography over silica gel

Sources & evidence

ORD record
ord-a9ff6cf5cef8404a89a1dec3cc52c390
Source dataset
uspto-grants-2015_08
Patent number
US09108983B2

Reaction notes

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