Hydrochloric Acid → HCID 178493119, compound

HRID 1060000Notes

Reaction equation

HRID 1060000 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][N:6]=[C:5]([C:9]2[CH:10]=[C:11]([NH:15][C:16]([NH2:18])=[S:17])[CH:12]=[CH:13][CH:14]=2)[CH:4]=1.[ClH:19].[C:20](OCC)(=O)C>CN(C)C=O.O1CCOCC1.IC>[ClH:19].[ClH:19].[CH3:1][O:2][C:3]1[CH:8]=[CH:7][N:6]=[C:5]([C:9]2[CH:10]=[C:11]([NH:15][C:16](=[NH:18])[S:17][CH3:20])[CH:12]=[CH:13][CH:14]=2)[CH:4]=1

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 18667488N-(3-(4-methoxypyridin-2-yl)phenyl)thiourea

Product 1

HCID 178493119HCID 178493119, compound

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 6328Methyl iodideSolventHCID 312751,4-DioxaneSolvent

Procedure

To a suspension of N-(3-(4-methoxypyridin-2-yl)phenyl)thiourea (122 mg) in N,N-dimethylformamide (2.5 ml) were added a solution of hydrogen chloride in 1,4-dioxane (4N, 0.25 ml) and iodomethane (0.156 ml), and the mixture was stirred at ambient temperature for 5 hours. Ethyl acetate (100 ml) was added to the mixture, and the mixture was cooled. The precipitate was collected by filtration. The precipitate was dissolved in water, and to the solution was added a saturated aqueous sodium hydrogencarbonate solution and extracted with dichloromethane. The organic layer was washed with brine, dried over sodium sulfate and evaporated under reduced pressure. The residue was dissolved in ethyl acetate, and to the solution was added a solution of hydrogen chloride in 1,4-dioxane (4N, 0.5 ml). The precipitate was collected by filtration and dried under reduced pressure to give N-(3-(4-methoxypyridin-2-yl)phenyl)-S-methylisothiourea dihydrochloride (153 mg).

Workup

  1. temperaturethe mixture was cooled
  2. filtrationThe precipitate was collected by filtration
  3. dissolutionThe precipitate was dissolved in water
  4. additionto the solution was added a saturated aqueous sodium hydrogencarbonate solution
  5. extractionextracted with dichloromethane
  6. washThe organic layer was washed with brine
  7. dry with materialdried over sodium sulfate
  8. customevaporated under reduced pressure
  9. dissolutionThe residue was dissolved in ethyl acetate
  10. additionto the solution was added a solution of hydrogen chloride in 1,4-dioxane (4N, 0.5 ml)
  11. filtrationThe precipitate was collected by filtration
  12. customdried under reduced pressure

Sources & evidence

ORD record
ord-82cc0208888647d1a915664e26061f26
Source dataset
uspto-grants-2003_02
Patent number
US06521643B1

Reaction notes

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