Iodoethane → HCID 45094698, compound

HRID 216615Notes

Reaction equation

HRID 216615 reaction equation
[NH2:1][C:2]1[NH:3][C:4]2[C:9]([C:10]=1[C:11]([NH2:13])=[O:12])=[CH:8][CH:7]=[CH:6][CH:5]=2.I[CH2:15][CH3:16].[H-].[Na+]>CN(C)C=O>[NH2:1][C:2]1[N:3]([CH2:15][CH3:16])[C:4]2[C:9]([C:10]=1[C:11]([NH2:13])=[O:12])=[CH:8][CH:7]=[CH:6][CH:5]=2

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 24758Sodium hydrideHCID 21862598HCID 21862598, compound2×

Product 1

HCID 45094698HCID 45094698, compoundYield 49%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Procedure

A solution of 2-aminoindole-3-carboxamide (Reference compound 18-1, 0.40 g, 2.3 mmol) in anhydrous N,N-dimethylformamide (2 mL) and a solution of iodoethane (0.20 mL, 2.5 mmol) in anhydrous N,N-dimethylformamide (2 mL) were successively added to a suspension of sodium hydride (purity 60%, 0.10 g, 2.5 mmol) in anhydrous N,N-dimethylformamide (10 mL) under ice-cooling. The mixture was stirred at room temperature for 1 hour. The reaction mixture was poured into ice-water (30 mL), and the whole was extracted with ethyl acetate (50 mL×2). The organic layer was washed with brine (30 mL), and dried over anhydrous magnesium sulfate. After the solvent was evaporated under reduced pressure, the residue was purified by silica gel column chromatography to give the title reference compound (0.22 g) as a brown solid (yield 49%).

Workup

  1. temperaturecooling
  2. extractionthe whole was extracted with ethyl acetate (50 mL×2)
  3. washThe organic layer was washed with brine (30 mL)
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customAfter the solvent was evaporated under reduced pressure
  6. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-a9f0136f595c4186a1f3dbab50de8609
Source dataset
uspto-grants-2012_06
Patent number
US08193237B2

Reaction notes

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