Methyl iodide → HCID 66613337, compound

HRID 76196Notes

Reaction equation

HRID 76196 reaction equation
[CH2:1]([O:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]#[C:11][C:12]2[CH:17]=[CH:16][C:15]([CH2:18][CH:19]([NH:21][C:22](=[O:24])[CH3:23])[CH3:20])=[CH:14][CH:13]=2)=[CH:6][CH:5]=1)[CH3:2].[Na].[H-].[Na+].[CH3:28]I>C1COCC1>[CH2:1]([O:3][C:4]1[CH:5]=[CH:6][C:7]([C:10]#[C:11][C:12]2[CH:17]=[CH:16][C:15]([CH2:18][CH:19]([N:21]([CH3:28])[C:22](=[O:24])[CH3:23])[CH3:20])=[CH:14][CH:13]=2)=[CH:8][CH:9]=1)[CH3:2]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 66610664HCID 66610664, compoundHCID 86584955HCID 86584955, compound

Product 1

HCID 66613337HCID 66613337, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

32.1 mg (100 μmol) N-{2-[4-(4-ethoxy-phenylethynyl)-phenyl]-1-methyl-ethyl}-acetamide are added to an ice cooled mixture of 40.0 mg (1.00 mmol) sodium NaH and 2.50 mL THF. The reaction mixture is stirred at 0° C. for 10 min. Then 25.0 μL (0.40 mmol) methyliodide are added dropwise and the mixture is stirred at r.t. for 2 h. The reaction is quenched by the addition of water and sat. NH4Cl solution, and is extracted with DCM. The organic layer is separated and the solvent is removed in vacuo. The residue is lyophilised from ACN/water.

Workup

  1. temperaturecooled
  2. stirringthe mixture is stirred at r.t. for 2 h
  3. customThe reaction is quenched by the addition of water and sat. NH4Cl solution
  4. extractionis extracted with DCM
  5. customThe organic layer is separated
  6. customthe solvent is removed in vacuo

Sources & evidence

ORD record
ord-1c0c998f35044826ae4c4fefe3fd45ed
Source dataset
uspto-grants-2014_09
Patent number
US08835472B2

Reaction notes

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