Water → HCID 86606595, compound

HRID 902582Notes

Reaction equation

HRID 902582 reaction equation
[CH2:1]([C:5]1[CH:14]=[CH:13][CH:12]=[C:11]2[C:6]=1[CH:7]=[CH:8][C:9]([NH:19][CH3:20])=[C:10]2[S:15](O)(=[O:17])=[O:16])[CH2:2][CH2:3][CH3:4].P(Cl)(Cl)(Cl)(Cl)[Cl:22].O.C(=O)([O-])O.[Na+]>C(OCC)(=O)C>[CH2:1]([C:5]1[CH:14]=[CH:13][CH:12]=[C:11]2[C:6]=1[CH:7]=[CH:8][C:9]([NH:19][CH3:20])=[C:10]2[S:15]([Cl:22])(=[O:17])=[O:16])[CH2:2][CH2:3][CH3:4]

Participants

6

Reactant 4

HCID 962WaterHCID 24819Phosphorus pentachlorideHCID 516892Sodium BicarbonateHCID 86606596HCID 86606596, compound

Product 1

HCID 86606595HCID 86606595, compoundYield 82.4%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

2 (23.9 g, 0.081 mol) was cooled with ice under nitrogen and mixed with phosphorus pentachloride (18.7 g, 0.0896 mol). The mixture was heated on a water bath at 60° C. for 2 hours and poured into a mixture of ice (164 g) and water (341 g). Ethyl acetate (400 mL) and sodium hydrogen carbonate (50 g, 0.60 mol) were added. The phases were separated and the water phase was extracted with ethyl acetate. The combined organic phases were washed, dried (sodium sulphate), and treated with activated carbon (1.1 g). Evaporation of the solvent gave 20.8 g of 3 as an oil. The product can be purified by chromatography.

Workup

  1. customThe phases were separated
  2. extractionthe water phase was extracted with ethyl acetate
  3. washThe combined organic phases were washed
  4. dry with materialdried (sodium sulphate)
  5. additiontreated with activated carbon (1.1 g)
  6. customEvaporation of the solvent

Sources & evidence

ORD record
ord-efbfb0f10cd64b1daba9694ef10323d1
Source dataset
uspto-grants-2008_04
Patent number
US07365223B2

Reaction notes

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