Potassium Carbonate → (R)-(1-Methyl-2,2,2-trifluoroethyl)-thiourea

HRID 1191079Notes

Reaction equation

HRID 1191079 reaction equation
C([NH:9][C:10]([NH:12][C@H:13]([CH3:18])[C:14]([F:17])([F:16])[F:15])=[S:11])(=O)C1C=CC=CC=1.C(=O)([O-])[O-].[K+].[K+]>CO.O>[CH3:18][C@@H:13]([NH:12][C:10]([NH2:9])=[S:11])[C:14]([F:17])([F:16])[F:15]

Participants

5

Reactant 2

HCID 11430Potassium CarbonateHCID 58495475(R)-1-Benzoyl-3-(1-methyl-2,2,2-trifluoroethyl)-thiourea

Product 1

HCID 58495653(R)-(1-Methyl-2,2,2-trifluoroethyl)-thioureaYield 74.9%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

Dissolve (R)-1-benzoyl-3-(1-methyl-2,2,2-trifluoroethyl)-thiourea (6.2 g, 22.5 mmol) in methanol and add a solution of potassium carbonate (13.8 g, 100 mmol) in water (30 mL). Stir vigorously at room temperature overnight. Evaporate to dryness, dissolve residue in hot water (ca. 100 mL) and filter the resulting white crystals. Cool filtrate to 0° C., seed with crystals from hot water filtration, filter and collect resulting white crystals to obtain the desired intermediate (2.9 g, 74%). MS (ES+) m/z: 173 (M+H)+.

Workup

  1. customEvaporate to dryness
  2. dissolutiondissolve residue in hot water (ca. 100 mL)
  3. filtrationfilter the resulting white crystals
  4. filtrationCool filtrate to 0° C., seed with crystals from hot water filtration
  5. filtrationfilter
  6. customcollect
  7. customresulting white crystals

Sources & evidence

ORD record
ord-c717b8cd54c340759867ca97ec07b607
Source dataset
uspto-grants-2014_03
Patent number
US08680091B2

Reaction notes

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