Dimethylformamide → HCID 20265424, compound

HRID 463896Notes

Reaction equation

HRID 463896 reaction equation
[Cl:1][C:2]1[CH:20]=[CH:19][C:5]([C:6]([C:8]2[C:12]([NH:13][C:14](=O)CBr)=[C:11]([CH3:18])[O:10][N:9]=2)=O)=[CH:4][CH:3]=1.[H-].[Na+].CI.[C:25](=[O:28])(O)[O-].[Na+].[CH3:30][N:31](C)C=O>CCCCCC>[CH3:18][C:11]1[O:10][NH:9][C:8]2[C:12]=1[N:13]([CH3:14])[C:25](=[O:28])[CH:30]=[N:31][C:6]=2[C:5]1[CH:19]=[CH:20][C:2]([Cl:1])=[CH:3][CH:4]=1

Participants

7

Reactant 5

HCID 6228Dimethylformamide2×HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 516892Sodium BicarbonateHCID 13424156HCID 13424156, compound

Product 1

HCID 20265424HCID 20265424, compound

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Conditions

Temperature
20 °C

Procedure

A solution of N-[3-(4-chlorobenzoyl)-5-methylisoxazol-4-yl]-bromoacetamide of Example Vc (4.26 g, 15.5 mmoles) in dimethylformamide (DMF) (40 ml) was added to a suspension of hexane-washed sodium hydride (0.67 g, 14 mmoles, 50% oil dispersion) in DMF (40 ml) at 5° C. After warming to 20° C., methyl iodide (1.06 ml, 17 mmoles) was added. The reaction solution was Poured into dilute sodium bicarbonate (600 ml) with stirring. The precipitate was extracted with ethyl acetate, the organic solution was washed with water, saturated sodium chloride, and dried (sodium sulfate). Concentration gave a residue (5.5 g) which was chromatographed by high pressure liquid chromatography (HPLC) (8% ethyl acetate:dichloromethane) to give a solid that was pulverized to yield 3.0 g (66%) of a powder, melting point 133°-145° C.

Workup

  1. extractionThe precipitate was extracted with ethyl acetate
  2. washthe organic solution was washed with water, saturated sodium chloride
  3. dry with materialdried (sodium sulfate)
  4. concentrationConcentration

Sources & evidence

ORD record
ord-ebe92f51a76447ac94b839ac6fa106ea
Source dataset
uspto-grants-1985_10
Patent number
US04544753

Reaction notes

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