Hydrochloric Acid → HCID 23532950, compound

HRID 617704Notes

Reaction equation

HRID 617704 reaction equation
[CH3:1][C:2]1[C:7]2[C:8]3([CH2:13][CH2:14]S[C:6]=2[C:5]([CH3:16])=[CH:4][C:3]=1[C:17]([OH:19])=[O:18])[O:12][CH2:11][CH2:10][O:9]3.C([O-])(=O)C.[Na+].O[O:26][S:27]([O-:29])=O.[K+].Cl>O.CO>[CH3:1][C:2]1[C:7]2[C:8]3([CH2:13][CH2:14][S:27](=[O:29])(=[O:26])[C:6]=2[C:5]([CH3:16])=[CH:4][C:3]=1[C:17]([OH:19])=[O:18])[O:12][CH2:11][CH2:10][O:9]3

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 517045Sodium AcetateHCID 21849004HCID 21849004, compoundHCID 23707502Potassium hydroxy sulfite

Product 1

HCID 23532950HCID 23532950, compoundYield 78.7%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent2×

Conditions

Temperature
0 °C

Procedure

4.73 g (0.017 mol) of the title compound of Step E and 2.08 g (0.025 mol) of sodium acetate were added to 85 mL of methanol. The solution was cooled to about 0° C., and a solution of 17.66 g (0.029 mol) of OXONE® (purchased from Aldrich Chemical Company) in 85 mL of water was added dropwise while keeping the temperature below 6° C. The mixture was warmed to room temperature and stirred under nitrogen overnight. The mixture was diluted with 50 mL of water, cooled to about 0° C., acidified to around pH 2 with concentrated hydrochloric acid, and then extracted with chloroform (3×150 mL). The combined organic layers were dried (MgSO4), filtered, and evaporated to dryness. The residue was triturated in diethyl ether:hexane (1:9) which was decanted to yield 4.18 g of the title compound of Step F as a solid melting at 185° C. (dec). 1H NMR (Me2SO-d6): δ2.35 (s,3H), 2.5 (m,2H), 2.6 (s,3H), 3.5 (m,2H), 4.16 (m,2H), 4.2 (m,2H), 7.6 (s,1H).

Workup

  1. customthe temperature below 6° C
  2. temperatureThe mixture was warmed to room temperature
  3. temperaturecooled to about 0° C.
  4. extractionextracted with chloroform (3×150 mL)
  5. dry with materialThe combined organic layers were dried (MgSO4)
  6. filtrationfiltered
  7. customevaporated to dryness
  8. customThe residue was triturated in diethyl ether:hexane (1:9) which
  9. customwas decanted

Sources & evidence

ORD record
ord-d4d3822376234370ba9d804d3feba7e5
Source dataset
uspto-grants-1999_09
Patent number
US05952266

Reaction notes

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