Sulfuric Acid → HCID 17930969, compound

HRID 900449Notes

Reaction equation

HRID 900449 reaction equation
CO[CH:3]=[CH:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][N:6]=1.[S:11](=O)(=O)(O)O.N1CCOCC1.[C:22]([CH2:24][C:25]([NH2:27])=[O:26])#[N:23].[S]>C(O)C.O>[NH2:23][C:22]1[S:11][C:4]([C:5]2[CH:10]=[CH:9][CH:8]=[CH:7][N:6]=2)=[CH:3][C:24]=1[C:25]([NH2:27])=[O:26]

Participants

8

Reactant 5

HCID 1118Sulfuric AcidHCID 7898CyanoacetamideHCID 8083MorpholineHCID 5362487SulfurHCID 53872785HCID 53872785, compound

Product 1

HCID 17930969HCID 17930969, compoundYield 17%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

2-(2-Methoxyvinyl)pyridine (1.28 g) was dissolved in ethanol (13 ml) and to the solution was added 6M sulphuric acid (3.6 ml). The solution was heated to 80° C. for 20 minutes then allowed to cool to 55° C. Morpholine (8 ml) was added followed by cyanoacetamide (0.796 g) and sulfur (0.334 g). The mixture was heated at 55° C. for 4 h. After cooling to room temperature the solution was poured into water (100 ml) and extracted with ethyl acetate. The extracts were dried (MgSO4), filtered and evaporated. The residue was adsorbed onto silica gel and eluted with 2-5% methanol in dichloromethane to give an orange solid (345 mg, 17%).

Workup

  1. temperatureto cool to 55° C
  2. temperatureThe mixture was heated at 55° C. for 4 h
  3. temperatureAfter cooling to room temperature the solution
  4. extractionextracted with ethyl acetate
  5. dry with materialThe extracts were dried (MgSO4)
  6. filtrationfiltered
  7. customevaporated
  8. washeluted with 2-5% methanol in dichloromethane

Sources & evidence

ORD record
ord-7f9442a79c6f4209abeb9b519bd0125c
Source dataset
uspto-grants-2008_04
Patent number
US07358376B2

Reaction notes

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