Methyl iodide → HCID 21833808, compound

HRID 1741090Notes

Reaction equation

HRID 1741090 reaction equation
[O:1]1[CH2:5][CH2:4][N:3]=[C:2]1[C:6]1[CH:11]=[CH:10][C:9]([C:12]2[CH:17]=[CH:16][C:15]([C:18]([OH:20])=[O:19])=[CH:14][CH:13]=2)=[C:8]([CH3:21])[CH:7]=1.[H-].[Na+].I[CH3:25]>CN(C=O)C.C(OCC)(=O)C>[O:1]1[CH2:5][CH2:4][N:3]=[C:2]1[C:6]1[CH:11]=[CH:10][C:9]([C:12]2[CH:13]=[CH:14][C:15]([C:18]([O:20][CH3:25])=[O:19])=[CH:16][CH:17]=2)=[C:8]([CH3:21])[CH:7]=1

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 218338564'-(4,5-Dihydrooxazol-2-yl)-2'-methylbiphenyl-4-carboxylic acid

Product 1

HCID 21833808HCID 21833808, compoundYield 15.4%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

4'-(4,5-Dihydrooxazol-2-yl)-2'-methylbiphenyl-4-carboxylic acid (D113) (0.92 g, 3.3 mmol) was stirred under Ar in dry DMF (20 ml), and sodium hydride (80% in mineral oil, 0.15 g, 5.0 mmol) was added. This mixture was stirred for 30 min, and then treated with iodomethane (0.22 ml, 3.5 mmol). After a further 15 min, the mixture was diluted with ethyl acetate (200 ml), washed with water and brine, dried (Na2SO4) and evaporated. The crude product was purified by chromatography on silica gel, eluting with 0-2% methanol/dichloromethane. This gave the title compound (0.15 g, 15%) as a white solid.

Workup

  1. waitAfter a further 15 min
  2. washwashed with water and brine
  3. dry with materialdried (Na2SO4)
  4. customevaporated
  5. customThe crude product was purified by chromatography on silica gel
  6. washeluting with 0-2% methanol/dichloromethane

Sources & evidence

ORD record
ord-96235dbdae7b40bab0facbd1a9a196f6
Source dataset
uspto-grants-1999_10
Patent number
US05972951

Reaction notes

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