Water → HCID 18509409, compound

HRID 1356810Notes

Reaction equation

HRID 1356810 reaction equation
[CH3:1][C:2]([CH3:23])([CH3:22])[C:3]#[C:4]/[CH:5]=[CH:6]/[CH2:7][N:8]([CH2:10][C:11]1[CH:12]=[C:13]([C:18](O)([CH3:20])[CH3:19])[CH:14]=[CH:15][C:16]=1[CH3:17])[CH3:9].P(Cl)(Cl)(Cl)=O.O.[OH-].[Na+]>N1C=CC=CC=1>[CH3:1][C:2]([CH3:23])([CH3:22])[C:3]#[C:4]/[CH:5]=[CH:6]/[CH2:7][N:8]([CH2:10][C:11]1[CH:12]=[C:13]([C:18]([CH3:20])=[CH2:19])[CH:14]=[CH:15][C:16]=1[CH3:17])[CH3:9]

Participants

6

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 24813Phosphorus oxychlorideHCID 18509459HCID 18509459, compound

Product 1

HCID 18509409HCID 18509409, compoundYield 85.7%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
135 °C

Procedure

Compound 33 (520 mg; 1.66 mmol) was dissolved in pyridine (6 ml), and phosphorus oxychloride (1.27 g; 8.3 mmol) was added thereto. The mixture was stirred for 1 hour at 130-140° C., and then cooled. The reaction mixture was poured into water, and alkalinized with sodium hydroxide pellet. The mixture was extracted with ether (120 ml), and dried over magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=20:1), to thereby yield 420 mg of the target compound (yield: 85.7%).

Workup

  1. temperaturecooled
  2. extractionThe mixture was extracted with ether (120 ml)
  3. dry with materialdried over magnesium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. customthe residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=20:1)

Sources & evidence

ORD record
ord-b8a87f0af27742d1bf7aa592ca0f257b
Source dataset
uspto-grants-2003_07
Patent number
US06586633B1

Reaction notes

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