Methyl iodide → HCID 90418757, compound

HRID 1428922Notes

Reaction equation

HRID 1428922 reaction equation
[F:1][C:2]([F:17])([F:16])[C:3]([NH:5][C:6]1[CH:15]=[CH:14][C:9]2[N:10]=[C:11]([CH3:13])[O:12][C:8]=2[CH:7]=1)=[O:4].[C:18]([O-])([O-])=O.[K+].[K+].IC>CN(C=O)C.O>[F:17][C:2]([F:1])([F:16])[C:3]([N:5]([CH3:18])[C:6]1[CH:15]=[CH:14][C:9]2[N:10]=[C:11]([CH3:13])[O:12][C:8]=2[CH:7]=1)=[O:4]

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 1473012HCID 1473012, compound

Product 1

HCID 90418757HCID 90418757, compoundYield 104.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of 2,2,2-trifluoro-N-(2-methylbenzo[d]oxazol-6-yl)acetamide (15.0 g, 61.2 mmol) in DMF (100 mL) was treated with K2CO3 (8.448 g, 61.2 mmol) and the reaction mixture was stirred at rt for 1 h, then cooled to 0° C. Iodomethane (3.9 mL, 64.2 mmol) was added dropwise and stirring continued at rt overnight. The reaction mixture was diluted with water (100 mL) and extracted with EtOAc (3×100 mL). The organics were washed with brine, dried over Na2SO4 and concentrated to obtain crude 2,2,2-trifluoro-N-methyl-N-(2-methylbenzo[d]oxazol-6-yl)acetamide (16.5 g), (MS: ESI +ve, 259.26 [M+H]).

Workup

  1. temperaturecooled to 0° C
  2. stirringstirring
  3. waitcontinued at rt overnight
  4. extractionextracted with EtOAc (3×100 mL)
  5. washThe organics were washed with brine
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-58ece3f94ade45e4aec9ddcfd5235079
Source dataset
uspto-grants-2015_01
Patent number
US08937178B2

Reaction notes

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