Sodium hydride → HCID 9950934, compound

HRID 1279221Notes

Reaction equation

HRID 1279221 reaction equation
[OH:1][CH:2]([C:6]([O:19][CH3:20])([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[C:3]([OH:5])=[O:4].[H-].[Na+].Cl[C:24]1[N:25]=[N:26][C:27]([CH3:30])=[CH:28][CH:29]=1>CN(C=O)C>[CH3:30][C:27]1[N:26]=[N:25][C:24]([O:1][CH:2]([C:6]([O:19][CH3:20])([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[C:3]([OH:5])=[O:4])=[CH:29][CH:28]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 2272543-Chloro-6-methylpyridazine2×HCID 98819472-hydroxy-3-methoxy-3,3-diphenylpropanoic acid

Product 1

HCID 9950934HCID 9950934, compoundYield 11.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Procedure

1.3 g (4.8 mmol) of 2-hydroxy-3-methoxy-3,3-diphenylpropionic acid dissolved in DMF were added dropwise to a suspension of 0.43 g of NaH (14.3 mmol, 80% in white oil) in 10 ml of DMF. After stirring to room temperature for 30 minutes, the mixture was treated with 0.6 g (4.8 mmol) of 3-chloro-6-methylpyridazine in 10 ml of DMF and stirred overnight at room temperature. To complete the reaction, 0.6 g (4.8 mmol) of 3-chloro-6-methylpyridazine were then added again and the mixture was kept at 60° C. for 5 hours. It was poured onto ice water, extracted three times with ethyl acetate, the aqueous phase was brought to pH 2 with half-concentrated hydrochloric acid and the precipitate which was deposited was extracted with ethyl acetate. These ethyl acetate phases were dried with magnesium sulfate and then filtered and the solvent was stripped off under reduced pressure. 800 mg of the brown residue (1.19 g) were purified by means of MPLC, it being possible to isolate 199 mg of the desired product as a white solid.

Workup

  1. stirringstirred overnight at room temperature
  2. additionwere then added again
  3. waitthe mixture was kept at 60° C. for 5 hours
  4. additionIt was poured onto ice water
  5. extractionextracted three times with ethyl acetate
  6. extractionthe precipitate which was deposited was extracted with ethyl acetate
  7. dry with materialThese ethyl acetate phases were dried with magnesium sulfate
  8. filtrationfiltered
  9. custom800 mg of the brown residue (1.19 g) were purified by means of MPLC, it

Sources & evidence

ORD record
ord-c85552a2974841478bd10981163c73e8
Source dataset
uspto-grants-2002_09
Patent number
US06448248B1

Reaction notes

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