Hydrochloric Acid → N-(3-(4-methylpyridin-2-yl)phenyl)thiourea

HRID 1059987Notes

Reaction equation

HRID 1059987 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([C:8]2[CH:9]=[C:10]([NH:14][C:15]([NH:17]C(=O)C3C=CC=CC=3)=[S:16])[CH:11]=[CH:12][CH:13]=2)[CH:3]=1.[OH-].[Na+].Cl>CO.O>[CH3:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([C:8]2[CH:9]=[C:10]([NH:14][C:15]([NH2:17])=[S:16])[CH:11]=[CH:12][CH:13]=2)[CH:3]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 18667641N-(3-(4-methylpyridin-2-yl)phenyl)-N'-benzoylthiourea

Product 1

HCID 18667523N-(3-(4-methylpyridin-2-yl)phenyl)thioureaYield 94.1%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

To a suspension of N-(3-(4-methylpyridin-2-yl)phenyl)-N′-benzoylthiourea (540 mg) in methanol (5 ml) was added an aqueous sodium hydroxide solution (1N, 1.55 ml) dropwise. The mixture was stirred at 60° C. for 1 hour, cooled to ambient temperature, and the pH was adjusted to 8.0 with 1N hydrochloric acid. The mixture was diluted with water (50 ml) and extracted with ethyl acetate. The organic layer was washed with brine, dried over sodium sulfate and evaporated under reduced pressure. The residue was triturated with diisopropyl ether, collected by filtration, washed with diisopropyl ether and dried under reduced pressure to give N-(3-(4-methylpyridin-2-yl)phenyl)thiourea (356 mg).

Workup

  1. temperaturecooled to ambient temperature
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with brine
  4. dry with materialdried over sodium sulfate
  5. customevaporated under reduced pressure
  6. customThe residue was triturated with diisopropyl ether
  7. filtrationcollected by filtration
  8. washwashed with diisopropyl ether
  9. customdried under reduced pressure

Sources & evidence

ORD record
ord-7eea0902bb2d43e8b36311900fbaafa7
Source dataset
uspto-grants-2003_02
Patent number
US06521643B1

Reaction notes

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