Methyl iodide → HCID 58495512, compound

HRID 1191031Notes

Reaction equation

HRID 1191031 reaction equation
[H-].[Na+].[CH3:3][C:4]([CH3:17])([CH3:16])[C:5]([NH:7][C:8]1[CH:15]=[CH:14][C:11]([C:12]#[N:13])=[CH:10][CH:9]=1)=[O:6].[CH3:18]I>CN(C=O)C>[CH3:18][N:7]([C:5](=[O:6])[C:4]([CH3:17])([CH3:16])[CH3:3])[C:8]1[CH:15]=[CH:14][C:11]([C:12]#[N:13])=[CH:10][CH:9]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 4927441HCID 4927441, compound

Product 1

HCID 58495512HCID 58495512, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Add sodium hydride (0.21 g, 8.6 mmol, 95%) to a solution of 4-(2,2-dimethyl-propionylamino)-benzonitrile (1.589 g, 7.857 mmol) in anhydrous DMF (16 mL) at 0° C. under nitrogen. Add methyl iodide (0.54 mL, 8.6 mmol) after bubbling ceased (˜20 min) Stir the mixture to room temperature overnight. Partition the reaction mixture between DCM (250 mL) and water (100 mL). Wash the organic phase with water (2×100 mL). Dry over Na2SO4, filter and concentrate in vacuo. Purify the crude mixture by chromatography on silica gel eluting with hexane/EtOAc (1:0 to 1:1 gradient over 71 min; 50 mL/min) to obtain the desired intermediate as a white solid (1.201 g, 71%).

Workup

  1. custom(˜20 min)
  2. customPartition the reaction mixture between DCM (250 mL) and water (100 mL)
  3. washWash the organic phase with water (2×100 mL)
  4. dry with materialDry over Na2SO4
  5. filtrationfilter
  6. concentrationconcentrate in vacuo
  7. customPurify the crude mixture by chromatography on silica gel eluting with hexane/EtOAc (1:0 to 1:1 gradient over 71 min; 50 mL/min)

Sources & evidence

ORD record
ord-a8a76785192b42f38600750373e8a263
Source dataset
uspto-grants-2014_03
Patent number
US08680091B2

Reaction notes

Loading…