Hydrochloric Acid → HCID 178477464, compound

HRID 1059994Notes

Reaction equation

HRID 1059994 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]([CH3:19])=[C:13]([NH:15][C:16]([NH2:18])=[S:17])[CH:14]=2)[CH:4]=1.[ClH:20].[C:21](OCC)(=O)[CH3:22]>CN(C)C=O.O1CCOCC1.ICC>[ClH:20].[ClH:20].[CH3:1][O:2][C:3]1[CH:8]=[CH:7][N:6]=[C:5]([C:9]2[CH:10]=[CH:11][C:12]([CH3:19])=[C:13]([NH:15][C:16](=[NH:18])[S:17][CH2:21][CH3:22])[CH:14]=2)[CH:4]=1

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 18631029HCID 18631029, compound

Product 1

HCID 178477464HCID 178477464, compound

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 6340IodoethaneSolventHCID 312751,4-DioxaneSolvent

Procedure

To a suspension of N-(5-(4-methoxypyridin-2-yl)-2-methylphenyl)-thiourea (0.15 g) in N,N-dimethylformamide (3 ml) were added a solution of hydrogen chloride in 1,4-dioxane (4N, 0.274 ml) and iodoethane (0.22 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 ethyl acetate. 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-(5-(4-methoxypyridin-2-yl)-2-methylphenyl)-S-ethylisothiourea dihydrochloride (168 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 ethyl acetate
  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-2ec101e14db14eedb6522ccc5e421b82
Source dataset
uspto-grants-2003_02
Patent number
US06521643B1

Reaction notes

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