Phosphorus pentachloride → HCID 15219347, compound

HRID 2380658Notes

Reaction equation

HRID 2380658 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]2[C:8]3[C:12]([CH:15]([CH3:17])[CH3:16])([CH2:13][O:14][C:4]=2[CH:3]=1)[CH2:11][N:10]([C:18]([NH:20][C:21]1[CH:26]=[CH:25][C:24]([C:27]([F:30])([F:29])[F:28])=[CH:23][CH:22]=1)=O)[N:9]=3.P(Cl)(Cl)(Cl)(Cl)[Cl:32].C(=O)(O)[O-].[Na+]>C1C=CC=CC=1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]2[C:8]3[C:12]([CH:15]([CH3:17])[CH3:16])([CH2:13][O:14][C:4]=2[CH:3]=1)[CH2:11][N:10]([C:18]([Cl:32])=[N:20][C:21]1[CH:26]=[CH:25][C:24]([C:27]([F:30])([F:29])[F:28])=[CH:23][CH:22]=1)[N:9]=3

Participants

5

Reactant 3

HCID 24819Phosphorus pentachlorideHCID 516892Sodium BicarbonateHCID 18954838HCID 18954838, compound

Product 1

HCID 15219347HCID 15219347, compoundYield 7.3%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

To 0.50 g (0.0012 mol) of the product obtained in Step C in 20 mL of benzene was added 0.25 g (0.0012 mol) of phosphorous pentachloride. The reaction mixture was refluxed for 42 hours, cooled to room temperature, poured into a saturated solution of sodium bicarbonate (100 mL) and extracted with ethyl acetate (3×50 mL). The ethyl acetate was washed with brine (100 mL), dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure to afford an off-white solid. The solid was chromatographed on silica gel using ethyl acetate (15%) and hexanes (85%) as eluents which yielded 0.04 g of a white solid, mp 148° C. to 149° C.

Workup

  1. temperatureThe reaction mixture was refluxed for 42 hours
  2. extractionextracted with ethyl acetate (3×50 mL)
  3. washThe ethyl acetate was washed with brine (100 mL)
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customto afford an off-white solid
  8. customThe solid was chromatographed on silica gel

Sources & evidence

ORD record
ord-881c59b47e6e4c99800332d28f72b020
Source dataset
uspto-grants-1994_11
Patent number
US05369121

Reaction notes

Loading…