Methanesulfonic Acid → HCID 19610735, compound

HRID 1602193Notes

Reaction equation

HRID 1602193 reaction equation
Cl.[N:2]12[CH2:9][CH2:8][CH:5]([CH2:6][CH2:7]1)[C:4](=[O:10])[CH2:3]2.[CH2:11](S)[CH2:12][CH2:13][SH:14].CS(O)(=O)=O>C(O)(=O)C>[CH2:11]1[O:10][C:4]2([CH:5]3[CH2:8][CH2:9][N:2]([CH2:7][CH2:6]3)[CH2:3]2)[S:14][CH2:13][CH2:12]1

Participants

5

Reactant 3

HCID 6395Methanesulfonic AcidHCID 80131,3-PropanedithiolHCID 1020191-Azabicyclo(2.2.2)octan-3-one, hydrochloride (1:1)

Product 1

HCID 19610735HCID 19610735, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 3-quinuclidinone hydrochloride (10 g, 62 mmol), 1,3-propanedithiol (13.4 g, 124 mmol), acetic acid (40 ml), and methanesulfonic acid (2 ml) was refluxed overnight. Most of the acetic acid was evaporated, 200 ml of water was added, and the solution was washed twice with ether. The pH of the solution was adjusted to basic by the addition of 1 M aqueous sodium hydroxide and the product was extracted with two portions of ethyl acetate. Drying over magnesium sulfate and evaporation of the solvent gave the title compound (13.3 g, 61.9 mmol, 100%) as a colorless solid 71-72° C.

Workup

  1. temperaturewas refluxed overnight
  2. customMost of the acetic acid was evaporated
  3. addition200 ml of water was added
  4. washthe solution was washed twice with ether
  5. additionbasic by the addition of 1 M aqueous sodium hydroxide
  6. extractionthe product was extracted with two portions of ethyl acetate
  7. dry with materialDrying over magnesium sulfate and evaporation of the solvent

Sources & evidence

ORD record
ord-d29afeed90484caea95f5bda3add59bc
Source dataset
uspto-grants-1999_11
Patent number
US05981539

Reaction notes

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