Potassium Carbonate → [4-(2-Methyl-oxazol-5-yl)-phenyl]-thiourea

HRID 2076083Notes

Reaction equation

HRID 2076083 reaction equation
[CH3:1][C:2]1[O:3][C:4]([C:7]2[CH:12]=[CH:11][C:10]([NH2:13])=[CH:9][CH:8]=2)=[CH:5][N:6]=1.C([N:22]=[C:23]=[S:24])(=O)C1C=CC=CC=1.C(=O)([O-])[O-].[K+].[K+]>O1CCCC1.O>[CH3:1][C:2]1[O:3][C:4]([C:7]2[CH:12]=[CH:11][C:10]([NH:13][C:23]([NH2:22])=[S:24])=[CH:9][CH:8]=2)=[CH:5][N:6]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 68284Benzoyl isothiocyanateHCID 15187744-(2-Methyl-1,3-oxazol-5-yl)aniline

Product 1

HCID 86632608[4-(2-Methyl-oxazol-5-yl)-phenyl]-thioureaYield 17%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-(2-methyl-oxazol-5-yl)phenylamine (470 mg, 2.7 mmol, CAS 89260-50-4) in tetrahydrofurane (6 mL) was added drop wise under benzoyl isothiocyanate (402 uL, 2.8 mmol). The reaction was stirred at room temperature for 3 hours. The solvent was removed under reduced pressure. The residue was dissolved in methanol (7 mL) and a solution of potassium carbonate (1119 mg, 8.1 mmol) in water (3.6 mL) was added. A solid precipitated and the reaction was stirred over night at room temperature. The solvent was removed under reduced pressure. The residue was dissolved in methanol (20 mL), tetrahydrofurane (10 mL) and 1M aqueous sodium hydroxide solution (8.1 mL). The reaction was stirred over night at room temperature, diluted with water and extracted three times with methylene chloride. The combined organic layers were dried over sodium sulfate, filtered and the solvent was removed under reduced pressure. The residue was suspended in water and extracted three times with methylene chloride. The combined organic layers were washed with brine, dried over sodium sulfate, filtered and the solvent was removed under reduced pressure. The residue was purified on silica gel using methylene chloride and methylene chloride/methanol (19:1 v/v) as eluent to yield the title compound (105 mg, 17%) as a light brown solid. MS ISP (m/e): 234.2 (100) [(M+H)+]. 1H NMR (DMSO-D6, 300 MHz): δ (ppm)=9.79 (s, 1H), 7.59 (d, 1H), 7.52 (d, 2H), 7.45 (s, 1H), 2.47 (s, 3H).

Workup

  1. customThe solvent was removed under reduced pressure
  2. dissolutionThe residue was dissolved in methanol (7 mL)
  3. customA solid precipitated
  4. stirringthe reaction was stirred over night at room temperature
  5. customThe solvent was removed under reduced pressure
  6. dissolutionThe residue was dissolved in methanol (20 mL)
  7. stirringThe reaction was stirred over night at room temperature
  8. additiondiluted with water
  9. extractionextracted three times with methylene chloride
  10. dry with materialThe combined organic layers were dried over sodium sulfate
  11. filtrationfiltered
  12. customthe solvent was removed under reduced pressure
  13. extractionextracted three times with methylene chloride
  14. washThe combined organic layers were washed with brine
  15. dry with materialdried over sodium sulfate
  16. filtrationfiltered
  17. customthe solvent was removed under reduced pressure
  18. customThe residue was purified on silica gel

Sources & evidence

ORD record
ord-fea4698fe70c45de9c1226b15e592bb0
Source dataset
uspto-grants-2011_04
Patent number
US07923450B2

Reaction notes

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