Methyl iodide → HCID 68670760, compound

HRID 2071096Notes

Reaction equation

HRID 2071096 reaction equation
[CH3:1][O:2][CH:3]([O:22][CH3:23])[C:4]1[CH:5]=[C:6]([NH:14][C:15](=[O:21])[O:16][C:17]([CH3:20])([CH3:19])[CH3:18])[CH:7]=[C:8]([C:10]([F:13])([F:12])[F:11])[CH:9]=1.[H-].[Na+].[CH3:26]I>CN(C=O)C>[CH3:23][O:22][CH:3]([O:2][CH3:1])[C:4]1[CH:5]=[C:6]([N:14]([CH3:26])[C:15](=[O:21])[O:16][C:17]([CH3:19])([CH3:20])[CH3:18])[CH:7]=[C:8]([C:10]([F:13])([F:12])[F:11])[CH:9]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 68671204HCID 68671204, compound

Product 1

HCID 68670760HCID 68670760, compoundYield 85.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To tert-butyl 3-(dimethoxymethyl)-5-(trifluoromethyl)phenylcarbamate (125 mg, 0.37 mmol) in DMF (5 ml) at 0° C., sodium hydride (22 mg, 0.56 mmol) was added. After stirring at rt for 0.5 h, methyl iodide (263 mg, 1.85 mmol) was added and stirred overnight at rt. Reaction mixture was then cooled, quenched with methanol, extracted with ether. Organic layer was dried and evaporated and the crude residue was column purified (10% ethylacetate/90% hexanes) to yield 110 mg of tert-butyl 3-(dimethoxymethyl)-5-(trifluoromethyl)phenyl(methyl)carbamate.

Workup

  1. stirringstirred overnight at rt
  2. customReaction mixture
  3. temperaturewas then cooled
  4. customquenched with methanol
  5. extractionextracted with ether
  6. customOrganic layer was dried
  7. customevaporated
  8. custompurified (10% ethylacetate/90% hexanes)

Sources & evidence

ORD record
ord-031f88530d0047529a8d91074f6a9bf5
Source dataset
uspto-grants-2012_10
Patent number
US08299267B2

Reaction notes

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