Hydrochloric Acid → HCID 178477468, compound

HRID 1059992Notes

Reaction equation

HRID 1059992 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([C:8]2[CH:13]=[CH:12][C:11]([NH:14][C:15]([NH2:17])=[S:16])=[CH:10][CH:9]=2)[CH:3]=1.[ClH:18].C(=O)([O-])O.[Na+].O1CCO[CH2:26][CH2:25]1>CN(C)C=O.ICC>[ClH:18].[ClH:18].[CH3:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([C:8]2[CH:9]=[CH:10][C:11]([NH:14][C:15](=[NH:17])[S:16][CH2:25][CH3:26])=[CH:12][CH:13]=2)[CH:3]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 516892Sodium BicarbonateHCID 18630996HCID 18630996, compound

Product 1

HCID 178477468HCID 178477468, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6340IodoethaneSolvent

Conditions

Temperature
50 °C

Procedure

To a suspension of N-(4-(4-methylpyridin-2-yl)phenyl)thiourea (186 mg) in N,N-dimethylformamide(4 ml) were added a solution of hydrogen chloride in 1,4-dioxane (4N, 0.383 ml) and iodoethane (0.306 ml), and the mixture was stirred at 50° C. for 2.5 hours. After cooling, the mixture was poured into 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 recrystallized from ethanol-ethyl acetate to give N-(4-(4-methylpyridin-2-yl)phenyl)-S-ethylisothiourea dihydrochloride (162 mg).

Workup

  1. temperatureAfter cooling
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with brine
  4. dry with materialdried over sodium sulfate
  5. customevaporated under reduced pressure
  6. dissolutionThe residue was dissolved in ethyl acetate
  7. additionto the solution was added a solution of hydrogen chloride in 1,4-dioxane (4N, 0.5 ml)
  8. filtrationThe precipitate was collected by filtration
  9. customrecrystallized from ethanol-ethyl acetate

Sources & evidence

ORD record
ord-4ff61d869c0f4307baa6d2bb9a4432e7
Source dataset
uspto-grants-2003_02
Patent number
US06521643B1

Reaction notes

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