Methyl iodide → HCID 53922683, compound

HRID 1418362Notes

Reaction equation

HRID 1418362 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[NH:9][C:10](=[O:15])[C:11]([F:14])([F:13])[F:12])#[N:2].[H-].[Na+].[CH3:18]I>C1COCC1>[C:1]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[N:9]([CH3:18])[C:10](=[O:15])[C:11]([F:13])([F:12])[F:14])#[N:2]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 9203669HCID 9203669, compound

Product 1

HCID 53922683HCID 53922683, compoundYield 93.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

N-(2-Cyanophenyl)-2,2,2-trifluoroacetamide (3 g, 0.014 mol) was added to sodium hydride (60% in oil, 0.62 g, 0.026 mol) in THF (40 ml) under nitrogen and stirred for 4 h. Methyl iodide (8.7 ml, 0.14 mol) was added and stirring continued overnight. The mixture was poured onto brine and extracted with ethyl acetate, dried over sodium sulphate and evaporated to give the product (3 g), MS (+EI) 228 (M+). 1H NMR (CDCl3) 7.8 (1H, d), 7.7 (1H, dd), 7.4 (1H, dd), 7.4 (1H, d), 3.43 (3H, s).

Workup

  1. stirringstirring continued overnight
  2. additionThe mixture was poured onto brine
  3. extractionextracted with ethyl acetate
  4. dry with materialdried over sodium sulphate
  5. customevaporated

Sources & evidence

ORD record
ord-d4847f0527ba4fe6a942a99e84acd3b8
Source dataset
uspto-grants-1999_03
Patent number
US05883102

Reaction notes

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