Sodium Hydroxide → HCID 18509445, compound

HRID 1356853Notes

Reaction equation

HRID 1356853 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:22](O)([CH3:24])[CH3:23])[CH:5]=[C:6]([CH2:8][N:9]([CH2:11][C:12]2[CH:17]=[CH:16][C:15]([C:18]([CH3:21])([CH3:20])[CH3:19])=[CH:14][CH:13]=2)[CH3:10])[CH:7]=1.P(Cl)(Cl)(Cl)=O.[OH-].[Na+]>N1C=CC=CC=1>[C:18]([C:15]1[CH:14]=[CH:13][C:12]([CH2:11][N:9]([CH2:8][C:6]2[CH:5]=[C:4]([C:22]([CH3:24])=[CH2:23])[CH:3]=[C:2]([Br:1])[CH:7]=2)[CH3:10])=[CH:17][CH:16]=1)([CH3:21])([CH3:19])[CH3:20]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 24813Phosphorus oxychlorideHCID 18509489HCID 18509489, compound

Product 1

HCID 18509445HCID 18509445, compoundYield 61.6%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Compound 140 (3.11 g; 7.69 mmol) was dissolved in pyridine (50 ml). While the solution was stirred at room temperature, phosphorus oxychloride (11.8 g; 76.9 mmol) was added dropwise. After completion of the addition, the mixture was stirred for 3 hours at 120° C. The mixture was brought to room temperature, and poured into ice/water. The mixture was alkalinized with sodium hydroxide, and extracted with chloroform (150 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=20:1), to thereby yield 1.83 g of the target compound as pale yellow oily matter (yield: 61.6%).

Workup

  1. additionAfter completion of the addition
  2. stirringthe mixture was stirred for 3 hours at 120° C
  3. customwas brought to room temperature
  4. extractionextracted with chloroform (150 ml)
  5. washThe organic layer was washed with saturated aqueous sodium bicarbonate solution
  6. dry with materialwith saturated brine, and dried over sodium sulfate
  7. customThe solvent was evaporated under reduced pressure
  8. customthe residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=20:1)

Sources & evidence

ORD record
ord-7585123627b840e8a22c63bb105387b5
Source dataset
uspto-grants-2003_07
Patent number
US06586633B1

Reaction notes

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