Phosphorus oxychloride → HCID 66938827, compound

HRID 1893545Notes

Reaction equation

HRID 1893545 reaction equation
[CH2:1]([O:3][C:4](=[O:28])[CH2:5][N:6]([CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24])[C:7]1[CH:12]=[C:11]([C:13]([NH:15][NH:16][C:17]([O:19]C)=[O:18])=O)[CH:10]=[CH:9][C:8]=1[CH3:21])[CH3:2].P(Cl)(Cl)(Cl)=O>>[CH2:1]([O:3][C:4](=[O:28])[CH2:5][N:6]([CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24])[C:7]1[CH:12]=[C:11]([C:13]2[O:19][C:17](=[O:18])[NH:16][N:15]=2)[CH:10]=[CH:9][C:8]=1[CH3:21])[CH3:2]

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 66880651HCID 66880651, compound

Product 1

HCID 66938827HCID 66938827, compoundYield 59.3%

Conditions

Temperature
110 °C

Procedure

To the compound (3.67 g, 9.28 mmol) obtained in step A was added phosphorus oxychloride (30 g), and the mixture was stirred at 110° C. for 2.5 hr. After cooling to room temperature, the reaction mixture was poured into ice water, and the solution was extracted with ethyl acetate. The organic layer was washed with water, saturated aqueous sodium hydrogen carbonate and saturated brine, and dried over anhydrous magnesium sulfate. The insoluble material was filtered off, and the solution was concentrated under reduced pressure to give the title compound (2.00 g, yield 59%) as a colorless solid.

Workup

  1. temperatureAfter cooling to room temperature
  2. extractionthe solution was extracted with ethyl acetate
  3. washThe organic layer was washed with water, saturated aqueous sodium hydrogen carbonate and saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationThe insoluble material was filtered off
  6. concentrationthe solution was concentrated under reduced pressure

Sources & evidence

ORD record
ord-5a7733dcd9544bd88ae1216103c15db1
Source dataset
uspto-grants-2013_08
Patent number
US08513235B2

Reaction notes

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