Hydrochloric Acid → HCID 18631029, compound

HRID 1059993Notes

Reaction equation

HRID 1059993 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][N:6]=[C:5]([C:9]2[CH:10]=[CH:11][C:12]([CH3:27])=[C:13]([NH:15][C:16]([NH:18]C(=O)C3C=CC=CC=3)=[S:17])[CH:14]=2)[CH:4]=1.[OH-].[Na+].Cl>CO.O>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][N:6]=[C:5]([C:9]2[CH:10]=[CH:11][C:12]([CH3:27])=[C:13]([NH:15][C:16]([NH2:18])=[S:17])[CH:14]=2)[CH:4]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 18631007HCID 18631007, compound

Product 1

HCID 18631029HCID 18631029, compoundYield 90%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a suspension of N-(5-(4-methoxypyridin-2-yl)-2-methylphenyl)-N′-benzoylthiourea (0.27 g) in methanol (5 ml) was added an aqueous sodium hydroxide solution (IN, 0.89 ml) dropwise. The mixture was stirred at ambient temperature for 4 hours, and the pH was adjusted to 8.0 with 1N hydrochloric acid. The mixture was diluted with water (50 ml) and extracted with dichloromethane-methanol (4:1) three times. 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-(5-(4-methoxypyridin-2-yl)-2-methylphenyl)thiourea (176 mg).

Workup

  1. extractionextracted with dichloromethane-methanol (4:1) three times
  2. washThe organic layer was washed with brine
  3. dry with materialdried over sodium sulfate
  4. customevaporated under reduced pressure
  5. customThe residue was triturated with diisopropyl ether
  6. filtrationcollected by filtration
  7. washwashed with diisopropyl ether
  8. customdried under reduced pressure

Sources & evidence

ORD record
ord-40e7cc3a0e834a9b9a62eae077adf9c5
Source dataset
uspto-grants-2003_02
Patent number
US06521643B1

Reaction notes

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