Sulfuric Acid → HCID 20496705, compound

HRID 1074450Notes

Reaction equation

HRID 1074450 reaction equation
[H-].[Na+].CI.S1CCSC1=NC1C=CC(CCCCCCO)=CC=1.P([O-])([O-])(O)=O.[K+].[K+].P([O-])(O)(O)=O.[K+].S([O-])([O-])(=O)=S.[Na+].[Na+].[S:44]1[CH2:48][CH2:47][S:46][C:45]1=[N:49][C:50]1[CH:55]=[CH:54][C:53]([CH2:56][CH2:57][CH2:58][CH2:59][CH2:60][CH2:61][O:62][CH3:63])=[CH:52][CH:51]=1.[S:64](=[O:68])(=[O:67])([OH:66])[OH:65]>CN(C)C=O.C(OCC)C>[S:64]([OH:68])([OH:67])(=[O:66])=[O:65].[S:44]1[CH2:48][CH2:47][S:46][C:45]1=[N:49][C:50]1[CH:51]=[CH:52][C:53]([CH2:56][CH2:57][CH2:58][CH2:59][CH2:60][CH2:61][O:62][CH3:63])=[CH:54][CH:55]=1

Participants

10

Reactant 7

HCID 1118Sulfuric AcidHCID 6328Methyl iodideHCID 24477Sodium ThiosulfateHCID 24758Sodium hydrideHCID 13145722HCID 13145722, compoundHCID 13145723HCID 13145723, compoundHCID 21889592Monopotassium phosphate dipotassium phosphate

Product 1

HCID 20496705HCID 20496705, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolvent2×HCID 6228DimethylformamideSolvent2×

Procedure

To a mixture of 0.97 g of sodium hydride and 5.7 g of methyl iodide in 40 ml of dried dimethylformamide was added dropwise a solution of 2.4 g of 6-[4-(1,3-dithiolan-2-ylideneamino)phenyl]hexanol in 25 ml of dimethylformamide. The resulting mixture was stirred at room temperature for 16 hours and then poured into an aqueous solution containing 0.2 M potassium hydrogen phosphate/potassium dihydrogen phosphate buffer solution (pH 7) with a few crystals of sodium thiosulfate added. This aqueous mixture was extracted with diethyl ether and the organic extract was then washed with water and aqueous saturated sodium chloride solution and dried over magnesium sulfate. The solvent was then removed to leave a crude orange oil which was purified by flash chromatography using 15 cm of silica gel and ethyl acetate/hexane as the eluant. The yellow oil obtained was N-(1,3-dithiolan-2-ylidene)-4-(6-methoxyhexyl)-aniline and 1.76 g of the oil was dissolved in 75 ml of diethyl ether. To this solution was added dropwise a solution of 0.6 g of sulfuric acid in 35 ml of diethyl ether. When the addition was complete, the mixture was placed in the freezer. The precipitate which formed was separated by filtration and crystallized from acetonitrile to give N-(1,3-dithiolan-2-ylidene)-4-(6-methoxyhexyl)aniline dihydrogen sulfate as white crystals melting at about 141°-142.5° C.

Workup

  1. additionpoured into an aqueous solution
  2. additionadded
  3. extractionThis aqueous mixture was extracted with diethyl ether
  4. extractionthe organic extract
  5. washwas then washed with water and aqueous saturated sodium chloride solution
  6. dry with materialdried over magnesium sulfate
  7. customThe solvent was then removed
  8. customto leave a crude orange oil which
  9. customwas purified by flash chromatography
  10. customThe yellow oil obtained
  11. additionWhen the addition
  12. customThe precipitate which formed
  13. customwas separated by filtration
  14. customcrystallized from acetonitrile

Sources & evidence

ORD record
ord-50c13c0a0a274082bbe2eea8afdd642c
Source dataset
uspto-grants-1983_07
Patent number
US04391818

Reaction notes

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