Hydrochloric Acid → HCID 18630996, compound

HRID 1059991Notes

Reaction equation

HRID 1059991 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([C:8]2[CH:16]=[CH:15][C:11](C=NO)=[CH:10][CH:9]=2)[CH:3]=1.Cl.[NH2:18][C:19]([NH2:21])=[S:20].C(N(CC)CC)C>CN(C)C=O.O1CCOCC1.S([O-])(O[O-])(=O)=O.[K+].[K+].O1CCCC1.O>[CH3:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([C:8]2[CH:9]=[CH:10][C:11]([NH:18][C:19]([NH2:21])=[S:20])=[CH:15][CH:16]=2)[CH:3]=1

Participants

10

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 2723790ThioureaHCID 136388329HCID 136388329, compound

Product 1

HCID 18630996HCID 18630996, compoundYield 43.8%

Reagents, catalysts & solvents 5

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent2×HCID 312751,4-DioxaneSolventHCID 10313463Potassium peroxymonosulphateSolvent

Procedure

To a solution of 4-(4-methylpyridin-2-yl)benzaldehyde oxime (0.41 g) in N,N-dimethylformamide (2 ml) were added a solution of hydrogen chloride in 1,4-dioxane (4N, 1.06 ml) and potassium peroxymonosulfate (OXONE, 0.712 g). The reaction mixture was stirred for 1.5 hours, and to the mixture were added tetrahydrofuran (10 ml) and thiourea (0.176 g). Then to the resultant suspension was added a solution of triethylamine (0.673 ml) in tetrahydrofuran (2 ml) dropwise, and the mixture was stirred for 1 hour. The mixture was poured into water (100 ml) and extracted with ethyl acetate (100 ml). The separated aqueous layer was extracted with ethyl acetate (50 ml). The combined organic layer was washed with brine, dried over sodium sulfate and evaporated under reduced pressure. The residue was dissolved in tetrahydrofuran (5 ml), and to the solution was added aqueous ammonia (28%, 3 ml) dropwise. The mixture was diluted with ethyl acetate and washed with water and brine. The organic layer was dried over sodium sulfate and evaporated under reduced pressure. To the residue was added dichloromethane and diisopropyl ether, and the precipitate was collected by filtration and dried to give N-(4-(4-methylpyridin-2-yl)-phenyl)thiourea (206 mg).

Workup

  1. stirringthe mixture was stirred for 1 hour
  2. extractionextracted with ethyl acetate (100 ml)
  3. extractionThe separated aqueous layer was extracted with ethyl acetate (50 ml)
  4. washThe combined organic layer was washed with brine
  5. dry with materialdried over sodium sulfate
  6. customevaporated under reduced pressure
  7. dissolutionThe residue was dissolved in tetrahydrofuran (5 ml)
  8. additionto the solution was added aqueous ammonia (28%, 3 ml) dropwise
  9. additionThe mixture was diluted with ethyl acetate
  10. washwashed with water and brine
  11. dry with materialThe organic layer was dried over sodium sulfate
  12. customevaporated under reduced pressure
  13. additionTo the residue was added dichloromethane and diisopropyl ether
  14. filtrationthe precipitate was collected by filtration
  15. customdried

Sources & evidence

ORD record
ord-a6c7aa61f86449feb35ffaeee9ace741
Source dataset
uspto-grants-2003_02
Patent number
US06521643B1

Reaction notes

Loading…