Phosphorus oxychloride → HCID 66880488, compound

HRID 1893541Notes

Reaction equation

HRID 1893541 reaction equation
[CH2:1]([O:3][C:4](=[O:27])[CH2:5][N:6]([CH2:21][C:22]([O:24][CH2:25][CH3:26])=[O:23])[C:7]1[CH:12]=[C:11]([C:13]([NH:15][CH2:16][C:17](=[O:19])[CH3:18])=O)[CH:10]=[CH:9][C:8]=1[CH3:20])[CH3:2].P(Cl)(Cl)(Cl)=O>>[CH2:1]([O:3][C:4](=[O:27])[CH2:5][N:6]([CH2:21][C:22]([O:24][CH2:25][CH3:26])=[O:23])[C:7]1[CH:12]=[C:11]([C:13]2[O:19][C:17]([CH3:18])=[CH:16][N:15]=2)[CH:10]=[CH:9][C:8]=1[CH3:20])[CH3:2]

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 66881469HCID 66881469, compound

Product 1

HCID 66880488HCID 66880488, compoundYield 57%

Conditions

Temperature
120 °C

Procedure

To the compound (555 mg, 1.47 mmol) obtained in step A was added phosphorus oxychloride (8.00 g), and the mixture was stirred at 120° C. for 3 hr. The reaction mixture was cooled to room temperature and slowly added to ice water. The solution was extracted with ethyl acetate, and 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. The obtained oil was purified by silica gel chromatography (ethyl acetate-hexane) to give the title compound (0.30 g, yield 57%) as a yellow oil.

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. extractionThe solution was extracted with ethyl acetate
  3. washwashed 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
  7. customThe obtained oil was purified by silica gel chromatography (ethyl acetate-hexane)

Sources & evidence

ORD record
ord-561a34df940b4c949de7a08dd6fed2d8
Source dataset
uspto-grants-2013_08
Patent number
US08513235B2

Reaction notes

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