1,4-Dioxane → HCID 58542319, compound

HRID 1951901Notes

Reaction equation

HRID 1951901 reaction equation
[S:1]([NH2:5])([NH2:4])(=[O:3])=[O:2].N12CCCN=C1CCCCC2.O1CCOCC1.N[C:24]([C:36]1[CH:37]=[N:38][C:39]([Cl:42])=[CH:40][CH:41]=1)([CH3:35])[C:25]([C:27]1[CH:32]=[CH:31][C:30]([Cl:33])=[C:29]([F:34])[CH:28]=1)=O>C(OCC)(=O)C>[Cl:42][C:39]1[CH:40]=[CH:41][C:36]([C:24]2([CH3:35])[C:25]([C:27]3[CH:32]=[CH:31][C:30]([Cl:33])=[C:29]([F:34])[CH:28]=3)=[N:5][S:1](=[O:3])(=[O:2])[NH:4]2)=[CH:37][N:38]=1

Participants

6

Reactant 4

HCID 312751,4-DioxaneHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 82267Sulfamide2×HCID 58542350HCID 58542350, compound

Product 1

HCID 58542319HCID 58542319, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
95 °C

Procedure

A molecular sieve 4 A (4.5 g), sulfamide (2.75 g, 28.6 mmol), and 1,8-diazabicyclo[5.4.0]undec-7-ene (1.45 g, 9.52 mmol) were added to a dioxane (60 ml) solution of the compound (2.99 g, 9.55 mmol) obtained in Step 6 above and the resulting mixture was stirred under heating at 95° C. for 18 hours. Further sulfamide (2.75 g, 28.6 mmol) was added and the resulting mixture was stirred under heating for 24 hours. The reaction mixture was concentrated under reduced pressure and then the residue obtained was diluted with ethyl acetate, washed with 10% aqueous citric acid solution and saturated brine, and then dried over anhydrous magnesium sulfate. A diisopropyl ether/ethyl acetate mixed solvent was added to the residue obtained and the resulting precipitate was collected by filtration and dried to give the title compound (2.86 g, 80%) as a colorless solid.

Workup

  1. stirringthe resulting mixture was stirred
  2. temperatureunder heating for 24 hours
  3. concentrationThe reaction mixture was concentrated under reduced pressure
  4. customthe residue obtained
  5. washwashed with 10% aqueous citric acid solution and saturated brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. additionA diisopropyl ether/ethyl acetate mixed solvent was added to the residue
  8. customobtained
  9. filtrationthe resulting precipitate was collected by filtration
  10. customdried

Sources & evidence

ORD record
ord-a9f039185dbc49758ff7b06840417e88
Source dataset
uspto-grants-2013_03
Patent number
US08404691B2

Reaction notes

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