Thionyl Chloride → HCID 44197392, compound

HRID 1464903Notes

Reaction equation

HRID 1464903 reaction equation
O[CH:2]1[C:15]2[CH:14]=[C:13]3[C:8]([CH:9]=[CH:10][CH:11]=[CH:12]3)=[N:7][C:6]=2[C:5]2=[C:16]([Si:20]([CH3:23])([CH3:22])[CH3:21])[C:17](=[O:19])[CH2:18][CH:4]2[CH2:3]1.O=S(Cl)[Cl:26].C([O-])(O)=O.[Na+]>C(Cl)Cl>[Cl:26][CH:2]1[C:15]2[CH:14]=[C:13]3[C:8]([CH:9]=[CH:10][CH:11]=[CH:12]3)=[N:7][C:6]=2[C:5]2=[C:16]([Si:20]([CH3:23])([CH3:22])[CH3:21])[C:17](=[O:19])[CH2:18][CH:4]2[CH2:3]1

Participants

5

Reactant 3

HCID 24386Thionyl ChlorideHCID 516892Sodium BicarbonateHCID 44197258HCID 44197258, compound

Product 1

HCID 44197392HCID 44197392, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

The 5-hydroxy-1-trimethylsilanyl-3,3a,4,5-tetrahydro-2H-cyclopenta[c]acridin-2-one (323 mg, 1.00 mmol) is dissolved in 10 ml of freshly distilled DCM under an argon atmosphere at 0° C. SOCl2 (182 μl, 2.5 mmol) is then added dropwise to the reaction medium, which is stirred at 0° C. for 15 min. The reaction medium is then run into a saturated aqueous solution of NaHCO3, the aqueous phase is extracted with DCM and the resulting organic phase is rinsed with a saturated aqueous solution of NaCl, dried over Na2SO4, filtered and evaporated. The residue obtained is purified by flash chromatography.

Workup

  1. extractionthe aqueous phase is extracted with DCM
  2. washthe resulting organic phase is rinsed with a saturated aqueous solution of NaCl
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue obtained
  7. customis purified by flash chromatography

Sources & evidence

ORD record
ord-d25beac46b704cc593a48e55a305b684
Source dataset
uspto-grants-2015_04
Patent number
US08999955B2

Reaction notes

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