Trifluoroacetic acid → HCID 59591391, compound

HRID 1666579Notes

Reaction equation

HRID 1666579 reaction equation
FC(F)(F)[C:3]1[CH:4]=[C:5]([C:9]2([C:13]#[N:14])[CH2:12][CH2:11][CH2:10]2)[CH:6]=[CH:7][CH:8]=1.[NH:17]([C:19](=[S:21])[NH2:20])N.C(O)(C(F)(F)F)=O.C([O-])(O)=O.[Na+]>C(OCC)(=O)C>[C:5]1([C:9]2([C:13]3[S:21][C:19]([NH2:20])=[N:17][N:14]=3)[CH2:12][CH2:11][CH2:10]2)[CH:6]=[CH:7][CH:8]=[CH:3][CH:4]=1

Participants

6

Reactant 4

HCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 2723789ThiosemicarbazideHCID 224067101-[3-(Trifluoromethyl)phenyl]cyclobutane-1-carbonitrile

Product 1

HCID 59591391HCID 59591391, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

To a T-vial containing 1-[3-(trifluoromethyl)phenyl]cyclobutanecarbonitrile (1 eq) and hydrazinecarbothioamide (1 eq) was added TFA (1 eq) dropwise at rt. Then the mixture was heated to 60° C. for 2 hrs and cooled to rt. Ethyl acetate and aq. NaHCO3 were added and extracted with ethyl acetate twice, the organic layers combined, dried with MgSO4, and concentrated to give the desired product which was used directly in the next step.

Workup

  1. temperaturecooled to rt
  2. extractionextracted with ethyl acetate twice
  3. dry with materialdried with MgSO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-0b021ed8501a4e6e92a1af5e62742977
Source dataset
uspto-grants-2011_10
Patent number
US08044075B2

Reaction notes

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