Cyanamide → HCID 86624873, compound

HRID 1028173Notes

Reaction equation

HRID 1028173 reaction equation
[O:1]1[CH2:6][CH2:5][CH2:4][C:3](=O)[CH2:2]1.N1CCCC1.O.C1(C)C=CC([S:20](O)(=O)=O)=CC=1.[S].[N:26]#[C:27][NH2:28]>C1CCCCC1.CO>[S:20]1[C:4]2[CH2:5][CH2:6][O:1][CH2:2][C:3]=2[N:26]=[C:27]1[NH2:28]

Participants

8

Reactant 5

HCID 9864CyanamideHCID 31268PyrrolidineHCID 901092H-Pyran-3(4H)-one, dihydro-HCID 521998p-Toluenesulfonic acid monohydrateHCID 5362487Sulfur

Product 1

HCID 86624873HCID 86624873, compoundYield 974.2%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8078CyclohexaneSolvent

Procedure

To a solution of dihydro-2H-pyran-3(4H)-one (purchased from JW-Pharmlab) (5.0 g, 50 mmol) in cyclohexane (100 mL) were added pyrrolidine (4.3 mL, 52 mmol) and p-toluenesulfonic acid monohydrate (0.05 g). The reaction mixture was refluxed for 3 h with a Dean-Stark trap, cooled and concentrated. The residue was dissolved in methanol (80 mL) and then sulfur (1.66 g, 52 mmol) was added. To the mixture was added a solution of cyanamide (2.52 g, 52 mmol) in methanol (20 mL) at 0° C. The reaction mixture was stirred at room temperature overnight, filtered, concentrated and purified by column chromatography using an Analogix® IT280™ (SiO2, 0-5% methanol in dichloromethane) to afford 0.4 g (5%) of the title compound. MS (ESI+) m/z 157 (M+H)+.

Workup

  1. temperatureThe reaction mixture was refluxed for 3 h with a Dean-Stark trap
  2. temperaturecooled
  3. concentrationconcentrated
  4. dissolutionThe residue was dissolved in methanol (80 mL)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. custompurified by column chromatography

Sources & evidence

ORD record
ord-f114c3119d0a4a8c90b232b918ad03e3
Source dataset
uspto-grants-2014_05
Patent number
US08735434B2

Reaction notes

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