Ethyl Acetate → HCID 86662650, compound

HRID 406334Notes

Reaction equation

HRID 406334 reaction equation
Br[CH:2]1[CH2:7][CH2:6][CH2:5][CH:4]([C:8]2[CH:13]=[CH:12][C:11]([C:14]([F:17])([F:16])[F:15])=[CH:10][CH:9]=2)[C:3]1=O.[NH2:19][C:20]([NH2:22])=[S:21].C(=O)(O)[O-].[Na+].C(OCC)(=O)C>C(O)C>[F:15][C:14]([F:17])([F:16])[C:11]1[CH:12]=[CH:13][C:8]([CH:4]2[C:3]3[N:19]=[C:20]([NH2:22])[S:21][C:2]=3[CH2:7][CH2:6][CH2:5]2)=[CH:9][CH:10]=1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 516892Sodium BicarbonateHCID 2723790ThioureaHCID 66618931HCID 66618931, compound

Product 1

HCID 86662650HCID 86662650, compoundYield 84.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The diastereomer mixture of 2-bromo-6-(4-trifluoromethylphenyl)cyclohexanone (500 mg) was dissolved in ethanol (10 mL). Thiourea (130 mg) was added and the mixture was stirred at room temperature overnight. A sodium bicarbonate solution and ethyl acetate were added to the reaction solution, and the organic layer was separated. The resulting organic layer was washed with brine and then dried over anhydrous sodium sulfate. The drying agent was separated by filtration, and then the organic layer was concentrated under reduced pressure. The residue was purified by silica gel column chromatography to obtain the title compound (394 mg).

Workup

  1. customthe organic layer was separated
  2. washThe resulting organic layer was washed with brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe drying agent was separated by filtration
  5. concentrationthe organic layer was concentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-1dc938f383d442b7b9fbe1ac454c3505
Source dataset
uspto-grants-2014_06
Patent number
US08754100B2

Reaction notes

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