Methyl iodide → HCID 58181088, compound

HRID 469339Notes

Reaction equation

HRID 469339 reaction equation
[H-].[Na+].[F:3][C:4]1[CH:5]=[C:6]([CH:20]=[C:21]([F:23])[CH:22]=1)[C:7]([C:9]1[CH:18]=[C:17]([CH3:19])[C:12]2[NH:13][C:14](=[O:16])[O:15][C:11]=2[CH:10]=1)=[O:8].I[CH3:25]>CN(C=O)C>[F:3][C:4]1[CH:5]=[C:6]([CH:20]=[C:21]([F:23])[CH:22]=1)[C:7]([C:9]1[CH:18]=[C:17]([CH3:19])[C:12]2[N:13]([CH3:25])[C:14](=[O:16])[O:15][C:11]=2[CH:10]=1)=[O:8]

Participants

5

Reactant 3

HCID 6328Methyl iodide2×HCID 24758Sodium hydrideHCID 58181203HCID 58181203, compound

Product 1

HCID 58181088HCID 58181088, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

0.349 g (8.00 mmol) sodium hydride (55%, suspension in mineral oil) were added at RT to 2.20 g (7.61 mmol) 6-(3,5-difluoro-benzoyl)-4-methyl-3H-benzoxazol-2-one in 10 mL DMF. The reaction mixture was stirred for 30 min at RT. Then 0.634 mL (10.0 mmol) iodomethane were added and the mixture was stirred for 1 h at RT. Then another 0.1 mL iodomethane were added and the mixture was stirred further at RT. After the addition of ice water the mixture was extracted with EtOAc. The organic phase was washed with water, dried on sodium sulphate and evaporated down i. vac. The residue was purified by flash chromatography. The fractions containing the product were combined, evaporated down and dried i. vac.

Workup

  1. stirringthe mixture was stirred for 1 h at RT
  2. stirringthe mixture was stirred further at RT
  3. extractionwas extracted with EtOAc
  4. washThe organic phase was washed with water
  5. customdried on sodium sulphate
  6. customevaporated down i
  7. customThe residue was purified by flash chromatography
  8. additionThe fractions containing the product
  9. customevaporated down
  10. customdried i

Sources & evidence

ORD record
ord-ebc4d512593b4f888cd7a10dd3d60475
Source dataset
uspto-grants-2014_01
Patent number
US08629137B2

Reaction notes

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