Hydrochloric Acid → HCID 178460857, compound

HRID 1060001Notes

Reaction equation

HRID 1060001 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(O[CH2:24][CH3:25])(=O)C.[CH3:26]N(C)C=O>O1CCOCC1.ICCC>[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][CH2:26][CH2:24][CH3:25])[CH:12]=[CH:13][CH:14]=2)[CH:4]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 6228DimethylformamideHCID 8857Ethyl AcetateHCID 18667488N-(3-(4-methoxypyridin-2-yl)phenyl)thiourea

Product 1

HCID 178460857HCID 178460857, compound

Reagents, catalysts & solvents 2

HCID 312751,4-DioxaneSolventHCID 336431-IodopropaneSolvent

Conditions

Temperature
50 °C

Procedure

To a suspension of N-(3-(4-methoxypyridin-2-yl)phenyl)thiourea (104 mg) in N,N-dimethylformamide (2 ml) were added a solution of hydrogen chloride in 1,4-dioxane (4N, 0.2 ml) and iodopropane (0.195 ml), and the mixture was stirred at 50° C. for 2 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-propylisothiourea dihydrochloride (143 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-ab00dd30f68e4ad0aea145b8cdb24fa1
Source dataset
uspto-grants-2003_02
Patent number
US06521643B1

Reaction notes

Loading…