Ammonium thiocyanate → HCID 59627506, compound

HRID 1623568Notes

Reaction equation

HRID 1623568 reaction equation
[CH2:1]([O:3][C:4](=[O:9])[CH2:5][C:6](Cl)=[O:7])[CH3:2].[NH4+].[N:11]#[C:12][S-:13].[F:14][C:15]1[CH:20]=[CH:19][C:18]([NH2:21])=[CH:17][C:16]=1[C:22]([F:25])([F:24])[F:23]>CC#N>[CH2:1]([O:3][C:4](=[O:9])[CH2:5][C:6]([NH:11][C:12]([NH:21][C:18]1[CH:19]=[CH:20][C:15]([F:14])=[C:16]([C:22]([F:25])([F:23])[F:24])[CH:17]=1)=[S:13])=[O:7])[CH3:2]

Participants

5

Reactant 3

HCID 15666Ammonium thiocyanateHCID 753774-Fluoro-3-(trifluoromethyl)anilineHCID 118931Ethyl 3-chloro-3-oxopropionate

Product 1

HCID 59627506HCID 59627506, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

3-Chloro-3-oxo-propanoic acid ethyl ester (5 g; 33.2 mmol) was slowly added to a stirred solution of thiocyanic acid, ammonium salt (1:1) (2.781 g; 36.5 mmol) in CH3CN (110 ml) at room temperature. After 2 hours, 4-fluoro-3-(trifluoromethyl)benzenamine (4.27 ml; 33.2 mmol) was added. The solvent was removed under reduced pressure. The resulting residue partitioned between H2O/DCM and the phases separated. The aqueous phase was extracted with DCM (×2) and the combined organic extracts were washed with brine, dried and filtered. Yield: 3.656 g of intermediate D15.

Workup

  1. customThe solvent was removed under reduced pressure
  2. customThe resulting residue partitioned between H2O/DCM
  3. customthe phases separated
  4. extractionThe aqueous phase was extracted with DCM (×2)
  5. washthe combined organic extracts were washed with brine
  6. customdried
  7. filtrationfiltered

Sources & evidence

ORD record
ord-7693fc5594d24aafa7296e927fe5dd9c
Source dataset
uspto-grants-2014_07
Patent number
US08778974B2

Reaction notes

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