Methyl Ethyl Ketone → HCID 19978264, compound

HRID 1449512Notes

Reaction equation

HRID 1449512 reaction equation
C(OC(=O)C[C:7]([CH3:10])([CH3:9])[CH3:8])(=O)C.S(Cl)([Cl:15])(=O)=O.[C:17](=[O:20])([O-])[OH:18].[Na+].[N:22]1[CH2:27][CH2:26][CH2:25][NH:24][C:23]=1[SH:28].[CH3:29][C:30]([CH2:32]C)=O>C(OCC)C>[ClH:15].[CH3:32][C:30]1[N:22]2[CH2:27][CH2:26][CH2:25][N:24]=[C:23]2[S:28][C:29]=1[C:17]([O:18][C:7]([CH3:8])([CH3:9])[CH3:10])=[O:20]

Participants

7

Reactant 5

HCID 6569Methyl Ethyl KetoneHCID 24648Sulfuryl chlorideHCID 516892Sodium BicarbonateHCID 19978254HCID 19978254, compoundHCID 178527864HCID 178527864, compound

Product 1

HCID 19978264HCID 19978264, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

In 300 ml of anhydrous diethylether was dissolved 31.6 g of tert-butylacetyl acetate and to the mixture was added dropwise 17.6 ml of sulfuryl chloride under cooling with ice. After stirring at room temperature for 30 minutes, the reaction mixture was added to the ice-cooled 5% sodium hydrogen-carbonate aqueous solution and an organic layer was washed with water. The organic layer was separated, dreid over anhydrous magnesium sulfate and the solvent was removed under reduced pressure to yield 37.8 g as an oily residue. This residue was dissolved in 500 ml of methylethylketone and to the solution was added 18.2 g of 3,4,5,6-tetrahydro-2-pyrimidinethiol, followed by reflux under heating for 12 hours. After cooling the reaction mixture, the precipitated crystals were collected by filtration. The crystals were washed successively with diethylether and acetone and suspended in 300 ml of isopropylalcohol. The suspension was refluxed under heating for 12 hours. The solvent was removed under reduced pressure. To the residue was added diethylether and the precipitated crystals were collected by filtration. The crystals were washed with acetone to yield 43.6 g of the titled compound.

Workup

  1. temperatureunder cooling with ice
  2. washan organic layer was washed with water
  3. customThe organic layer was separated
  4. customdreid over anhydrous magnesium sulfate and the solvent was removed under reduced pressure
  5. customto yield 37.8 g as an oily residue
  6. temperatureby reflux
  7. temperatureunder heating for 12 hours
  8. temperatureAfter cooling the reaction mixture
  9. filtrationthe precipitated crystals were collected by filtration
  10. washThe crystals were washed successively with diethylether and acetone
  11. temperatureThe suspension was refluxed
  12. temperatureunder heating for 12 hours
  13. customThe solvent was removed under reduced pressure
  14. additionTo the residue was added diethylether
  15. filtrationthe precipitated crystals were collected by filtration
  16. washThe crystals were washed with acetone

Sources & evidence

ORD record
ord-8b131984bb3f45b9bb33e252052274f6
Source dataset
uspto-grants-1997_02
Patent number
US05599813

Reaction notes

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