Perchloric Acid → HCID 23356734, compound

HRID 233665Notes

Reaction equation

HRID 233665 reaction equation
[CH3:1][CH:2]1[C:6](=[C:7]2SCCCS2)[CH2:5][C:4]2([CH2:17][CH2:16][N:15]([CH3:18])[CH2:14][CH2:13]2)[O:3]1.Cl(O)(=O)(=O)=[O:20].[C:24](=O)(O)[O-:25].[Na+]>CO.Cl[Hg]Cl>[CH3:1][CH:2]1[CH:6]([C:7]([O:25][CH3:24])=[O:20])[CH2:5][C:4]2([CH2:17][CH2:16][N:15]([CH3:18])[CH2:14][CH2:13]2)[O:3]1

Participants

6

Reactant 3

HCID 24247Perchloric AcidHCID 516892Sodium BicarbonateHCID 23356727HCID 23356727, compound

Product 1

HCID 23356734HCID 23356734, compound

Reagents, catalysts & solvents 2

HCID 24085Mercuric ChlorideCatalystHCID 887MethanolSolvent

Procedure

A suspension of 2,8-dimethyl-3-(1,3-dithian-2-ylidene)-1-oxa-8-azaspiro[4.5]decane (2.84 g, 9.95 mmol), HgCl2 (10.8 g, 0.04 mol) and perchloric acid (60%, 5.2 ml) in MeOH/85 ml) was heated at reflux for 2 hours, cooled and decomposed with saturated aqueous sodium bicarbonate solution. The solids were filtered and the filtrate was extracted with methylene chloride. The organic extracts were dried and evaporated. The residue obtained was chromatographed on silica gel and eluted with ammoniated 10-25% MeOH/CH2Cl2 to give the title ester as an oil (1.39 g). A 1 g sample of the oil was converted to the maleate salt in ether. The crude salt was crystallized from methylene chloride/ether to give the maleate salt of the title product (0.48 g), mp 105°-107° C.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 2 hours
  3. temperaturecooled
  4. filtrationThe solids were filtered
  5. extractionthe filtrate was extracted with methylene chloride
  6. customThe organic extracts were dried
  7. customevaporated
  8. customThe residue obtained
  9. customwas chromatographed on silica gel
  10. washeluted with ammoniated 10-25% MeOH/CH2Cl2

Sources & evidence

ORD record
ord-469c148f2de64afbbcfb4c5e23589f99
Source dataset
uspto-grants-1997_01
Patent number
US05594000

Reaction notes

Loading…