Water → HCID 13105764, compound

HRID 1632495Notes

Reaction equation

HRID 1632495 reaction equation
[O:1]=[C:2]1[CH:8](C)[O:7][CH:6]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2Cl)[C:5]2[CH:17]=[C:18](Cl)[CH:19]=[CH:20][C:4]=2[NH:3]1.C(=O)([O-])O.[Na+].P12(SP3(SP(SP(S3)(S1)=S)(=S)S2)=S)=S.O>O1CCCC1>[O:1]=[C:2]1[CH2:8][O:7][CH:6]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[C:5]2[CH:17]=[CH:18][CH:19]=[CH:20][C:4]=2[NH:3]1

Participants

6

Reactant 4

HCID 962WaterHCID 14817Phosphorus sulfide (P2S5)HCID 516892Sodium BicarbonateHCID 13105763HCID 13105763, compound

Product 1

HCID 13105764HCID 13105764, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of Compound 4 prepared in Example 1-(1) (3.45 g) and sodium hydrogencarbonate (5.5 g) in tetrahydrofuran (50 ml) is added phosphorus pentasulfide (5.5 g) at 50° C., and the mixture is refluxed for 1 hour, poured into water, and extracted with ethyl acetate. The organic layer is washed with saturated brine, dried over anhydrous sodium salfate, and concentrated under reduced pressure. The residue is purified on column chromatography (silica gel/methylene chloride). The resulting light yellow crystals are washed with n-hexane to give crystalline Compound 5 (3.1 g), which is recrystallized from ethyl acetate-n-hexane to give the title compound as pure crystals, mp. 193°-195° C.

Workup

  1. temperaturethe mixture is refluxed for 1 hour
  2. extractionextracted with ethyl acetate
  3. washThe organic layer is washed with saturated brine
  4. dry with materialdried over anhydrous sodium salfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue is purified on column chromatography (silica gel/methylene chloride)
  7. washThe resulting light yellow crystals are washed with n-hexane

Sources & evidence

ORD record
ord-7e61f857e57c45ba8698b65b3309fdd4
Source dataset
uspto-grants-1984_10
Patent number
US04476133

Reaction notes

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