Hydrochloric Acid → HCID 178477465, compound

HRID 1059996Notes

Reaction equation

HRID 1059996 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[C:12]([O:14][CH3:15])[CH:11]=[CH:10][N:9]=2)=[CH:4][C:3]=1[NH:16][C:17]([NH2:19])=[S:18].[ClH:20].[C:21](OCC)(=O)[CH3:22]>CN(C)C=O.O1CCOCC1.ICC>[ClH:20].[ClH:20].[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[C:12]([O:14][CH3:15])[CH:11]=[CH:10][N:9]=2)=[CH:4][C:3]=1[NH:16][C:17](=[NH:19])[S:18][CH2:21][CH3:22]

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 18631026HCID 18631026, compound

Product 1

HCID 178477465HCID 178477465, compound

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 6340IodoethaneSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
80 °C

Procedure

To a suspension of N-(2-fluoro-5-(4-methoxypyridin-2-yl)phenyl)-thiourea (0.1 g) in N,N-dimethylformamide (2 ml) were added a solution of hydrogen chloride in 1,4-dioxane (4N, 0.181 ml) and iodoethane (0.144 ml), and the mixture was stirred at 80° C. for 3 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, 1 ml). The precipitate was collected by filtration and dried under reduced pressure to give N-(2-fluoro-5-(4-methoxypyridin-2-yl)phenyl)-S-ethylisothiourea dihydrochloride (125 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, 1 ml)
  11. filtrationThe precipitate was collected by filtration
  12. customdried under reduced pressure

Sources & evidence

ORD record
ord-a0aa2a344db64f928eb24c07851455ab
Source dataset
uspto-grants-2003_02
Patent number
US06521643B1

Reaction notes

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