Sodium Sulfite → HCID 68710189, compound

HRID 1696708Notes

Reaction equation

HRID 1696708 reaction equation
CC[C@@H]1[C@@H]2C[C@H]([C@@H](OC3C4C(=CC=CC=4)C(O[C@@H](C4C=CN=C5C=4C=C(OC)C=C5)[C@@H]4N5C[C@H](CC)[C@@H](CC5)C4)=NN=3)C3C=CN=C4C=3C=C([O:22]C)C=C4)N(CC2)C1.CS(N)(=O)=O.C([Si]([O:71]/[C:72](/[C:75]1[CH:80]=[CH:79][C:78]([O:81][CH2:82][C:83]2[CH:88]=[CH:87][C:86]([O:89][CH3:90])=[CH:85][CH:84]=2)=[CH:77][CH:76]=1)=[CH:73]\[CH3:74])(C)C)(C)(C)C.S([O-])([O-])=O.[Na+].[Na+]>C(O)(C)(C)C.O>[OH:22][C@H:73]([CH3:74])[C:72]([C:75]1[CH:80]=[CH:79][C:78]([O:81][CH2:82][C:83]2[CH:88]=[CH:87][C:86]([O:89][CH3:90])=[CH:85][CH:84]=2)=[CH:77][CH:76]=1)=[O:71]

Participants

7

Reactant 4

HCID 24437Sodium SulfiteHCID 72879MethanesulfonamideHCID 112172021,4-Bis(dihydroquinidine)phthalazineHCID 67276589HCID 67276589, compound

Product 1

HCID 68710189HCID 68710189, compoundYield 89%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6386tert-ButanolSolvent

Procedure

Ad-mix-β (28.0 g) and methanesulfonamide (1.90 g, 20 mmol) were suspended in t-butanol (100 mL) and water (100 mL), then the compound (7.7 g, 20 mmol) synthesized in the above (2) was added under stirring with cooling with ice. The reaction solution was stirred for 15 hours with cooling with ice, then sodium sulfite (20 g, 0.16 mol) was added, and further stirred at room temperature for 1 hour. The reaction solution was poured in water, extracted with chloroform, and the organic layer was washed with saturated ammonium chloride and dried with magnesium sulfate. The solvent was removed under reduced pressure, and the resulting pale yellow solid was washed with diisopropyl ether and n-heptane to obtain the entitled compound (5.1 g, 89%) as a milky white solid.

Workup

  1. additionwas added
  2. temperaturewith cooling with ice
  3. stirringThe reaction solution was stirred for 15 hours
  4. temperaturewith cooling with ice
  5. stirringfurther stirred at room temperature for 1 hour
  6. extractionextracted with chloroform
  7. washthe organic layer was washed with saturated ammonium chloride
  8. dry with materialdried with magnesium sulfate
  9. customThe solvent was removed under reduced pressure
  10. washthe resulting pale yellow solid was washed with diisopropyl ether and n-heptane

Sources & evidence

ORD record
ord-40ca6fd5f49a475bb53cffa48b752b41
Source dataset
uspto-grants-2012_04
Patent number
US08163770B2

Reaction notes

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