Potassium Carbonate → 1-(2,2,2-Trifluoroethyl)thiourea

HRID 1191075Notes

Reaction equation

HRID 1191075 reaction equation
C([NH:9][C:10]([NH:12][CH2:13][C:14]([F:17])([F:16])[F:15])=[S:11])(=O)C1C=CC=CC=1.C(=O)([O-])[O-].[K+].[K+]>CO.O>[F:15][C:14]([F:17])([F:16])[CH2:13][NH:12][C:10]([NH2:9])=[S:11]

Participants

5

Reactant 2

HCID 11430Potassium CarbonateHCID 58495575HCID 58495575, compound

Product 1

HCID 202028121-(2,2,2-Trifluoroethyl)thioureaYield 66%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

Slurry 1-benzoyl-3-(2,2,2-trifluoroethyl)-thiourea (5.5 g, 21.2 mmol) and potassium carbonate (11.7 g, 84.7 mmol) in methanol (180 mL) and water (40 mL). Stir the mixture at room temperature for 16 h. Concentrate the solution in vacuo to a paste. Triturate with hot water (20 mL, 60° C.), filter off the solids, wash with water (20 mL, 25° C.) and hexane (excess). Collect the solids, slurry in EtOAc and concentrate in vacuo twice to remove residual water. Dry the material in a vacuum oven at 45° C. for 16 h to obtain the desired intermediate as an off-white solid (2.2 g, 66%). MS (ES+) m/z: 159.1 (M+H)+.

Workup

  1. concentrationConcentrate the solution in vacuo to a paste
  2. customTriturate with hot water (20 mL, 60° C.)
  3. filtrationfilter off the solids
  4. washwash with water (20 mL, 25° C.) and hexane (excess)
  5. customCollect the solids, slurry in EtOAc
  6. concentrationconcentrate in vacuo twice
  7. customto remove residual water
  8. customDry the material in a vacuum oven at 45° C. for 16 h

Sources & evidence

ORD record
ord-da0721c021574b16ad5c902124d32dfd
Source dataset
uspto-grants-2014_03
Patent number
US08680091B2

Reaction notes

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