Water → HCID 18408322, compound

HRID 1385962Notes

Reaction equation

HRID 1385962 reaction equation
[Cl:1][C:2]1[C:11]([C:12]2[C:13](=[O:23])[N:14]([CH3:22])[C:15]([C:18]([F:21])([F:20])[F:19])=[CH:16][CH:17]=2)=[CH:10][C:5]2[NH:6][C:7](=[O:9])[O:8][C:4]=2[CH:3]=1.[H-].[Na+].[CH2:26](Br)[C:27]#[CH:28].O>CN(C=O)C>[Cl:1][C:2]1[C:11]([C:12]2[C:13](=[O:23])[N:14]([CH3:22])[C:15]([C:18]([F:19])([F:20])[F:21])=[CH:16][CH:17]=2)=[CH:10][C:5]2[N:6]([CH2:28][C:27]#[CH:26])[C:7](=[O:9])[O:8][C:4]=2[CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7842Propargyl bromideHCID 24758Sodium hydrideHCID 18408345HCID 18408345, compound

Product 1

HCID 18408322HCID 18408322, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

0.20 g (0.58 mmol) of 3-(6-chlorobenzoxazolin-2-on-5-yl)-1-methyl-6-trifluoromethyl-2(1H)-pyridone was dissolved in 10 ml of DMF, and 0.026 g (0.65 mmol) of 60% sodium hydride was added thereto at room temperature, followed by stirring for 0.5 hour. Further, 0.09 g (0.76 mmol) of propargyl bromide was added thereto, followed by stirring at room temperature for 2 hours. After completion of the reaction, the reaction solution was poured into water and extracted with ethyl acetate. The organic layer was washed with water and dried over anhydrous magnesium sulfate. The organic layer was distilled off under reduced pressure, and the obtained residue was purified by silica gel column chromatography to obtain 0.17 g (yield: 78%) of the desired product. Melting point: 187-189° C. H-NMR (400 MHz, CDCl3) δ value: 2.38(1H,t), 3.72(3H,s,), 4.60(2H,d), 6.80(1H,d), 7.18(1H,s), 7.37(1H,s), 7.43(1H,d)ppm.

Workup

  1. customat room temperature
  2. stirringby stirring at room temperature for 2 hours
  3. customAfter completion of the reaction
  4. extractionextracted with ethyl acetate
  5. washThe organic layer was washed with water
  6. dry with materialdried over anhydrous magnesium sulfate
  7. distillationThe organic layer was distilled off under reduced pressure
  8. customthe obtained residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-59ffda25d936451aba5367138b02c511
Source dataset
uspto-grants-2001_07
Patent number
US06265349B1

Reaction notes

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