Sodium Carbonate → HCID 18509406, compound

HRID 1356855Notes

Reaction equation

HRID 1356855 reaction equation
[C:1]([C:4]1[CH:5]=[C:6]([C:24](O)([CH3:26])[CH3:25])[CH:7]=[C:8]([CH2:10][N:11]([CH2:13][C:14]2[CH:19]=[CH:18][C:17]([C:20]([CH3:23])([CH3:22])[CH3:21])=[CH:16][CH:15]=2)[CH3:12])[CH:9]=1)([CH3:3])=[CH2:2].P(Cl)(Cl)(Cl)=O.C(=O)([O-])[O-].[Na+].[Na+]>N1C=CC=CC=1>[C:20]([C:17]1[CH:16]=[CH:15][C:14]([CH2:13][N:11]([CH2:10][C:8]2[CH:9]=[C:4]([C:1]([CH3:3])=[CH2:2])[CH:5]=[C:6]([C:24]([CH3:26])=[CH2:25])[CH:7]=2)[CH3:12])=[CH:19][CH:18]=1)([CH3:23])([CH3:21])[CH3:22]

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 24813Phosphorus oxychlorideHCID 18509401HCID 18509401, compound

Product 1

HCID 18509406HCID 18509406, compoundYield 67.6%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Compound 142 (0.28 g; 7.66×10−1 mmol) and phosphorus oxychloride (0.59 g; 3.83 mmol) was added dropwise to pyridine (15 ml), and the mixture was refluxed for 2 hours. The mixture was brought to room temperature, and poured into ice/water. The pH of the mixture was adjusted to weak alkaline by use of sodium carbonate, followed by extraction with chloroform (50 ml). The organic layer was washed with saturated aqueous sodium bicarbonate solution and then with saturated brine, and dried over sodium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=5:1), to thereby yield 0.18 g of the target compound (yield: 67.6%).

Workup

  1. temperaturethe mixture was refluxed for 2 hours
  2. customwas brought to room temperature
  3. extractionfollowed by extraction with chloroform (50 ml)
  4. washThe organic layer was washed with saturated aqueous sodium bicarbonate solution
  5. dry with materialwith saturated brine, and dried over sodium sulfate
  6. customThe solvent was evaporated under reduced pressure
  7. customthe residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=5:1)

Sources & evidence

ORD record
ord-e81289335a664f6198dba6be1f7ea9b7
Source dataset
uspto-grants-2003_07
Patent number
US06586633B1

Reaction notes

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