Methyl iodide → 4-(3,4-Dimethyl-2-oxo-2,3-dihydro-benzoxazole-6-carbonyl)-2-fluoro-benzonitrile

HRID 469343Notes

Reaction equation

HRID 469343 reaction equation
[H-].[Na+].[F:3][C:4]1[CH:11]=[C:10]([C:12]([C:14]2[CH:23]=[C:22]([CH3:24])[C:17]3[NH:18][C:19](=[O:21])[O:20][C:16]=3[CH:15]=2)=[O:13])[CH:9]=[CH:8][C:5]=1[C:6]#[N:7].I[CH3:26]>CN(C=O)C>[CH3:26][N:18]1[C:17]2[C:22]([CH3:24])=[CH:23][C:14]([C:12]([C:10]3[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[C:4]([F:3])[CH:11]=3)=[O:13])=[CH:15][C:16]=2[O:20][C:19]1=[O:21]

Participants

5

Reactant 3

HCID 6328Methyl iodide2×HCID 24758Sodium hydrideHCID 581811882-Fluoro-4-(4-methyl-2-oxo-2,3-dihydro-benzoxazole-6-carbonyl)-benzonitrile

Product 1

HCID 581810894-(3,4-Dimethyl-2-oxo-2,3-dihydro-benzoxazole-6-carbonyl)-2-fluoro-benzonitrile

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

0.190 g (4.30 mmol) sodium hydride (55%, suspension in mineral oil) were added to 1.15 g (3.88 mmol) 2-fluoro-4-(4-methyl-2-oxo-2,3-dihydro-benzoxazole-6-carbonyl)-benzonitrile in 5.0 mL DMF at RT. The reaction mixture was stirred for 30 min at RT. Then 0.320 mL (5.00 mmol) iodomethane were added and the mixture was stirred for 1 h at RT. Then another 0.1 mL iodomethane were added and stirring was continued at RT. Ice water was added to the reaction mixture and the precipitate formed was suction filtered. The residue was purified by flash chromatography. The fractions containing the product were combined, evaporated down, triturated with diethyl ether, suction filtered and again washed with diethyl ether. The residue was dried i. vac.

Workup

  1. stirringthe mixture was stirred for 1 h at RT
  2. stirringstirring
  3. customwas continued at RT
  4. customthe precipitate formed
  5. filtrationfiltered
  6. customThe residue was purified by flash chromatography
  7. additionThe fractions containing the product
  8. customevaporated down
  9. customtriturated with diethyl ether, suction
  10. filtrationfiltered
  11. washagain washed with diethyl ether
  12. customThe residue was dried i

Sources & evidence

ORD record
ord-6fb9d739dacd4d8784ea181a1d35e6a6
Source dataset
uspto-grants-2014_01
Patent number
US08629137B2

Reaction notes

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