Iodoethane → HCID 59301393, compound

HRID 2236195Notes

Reaction equation

HRID 2236195 reaction equation
[OH:1][CH2:2][CH2:3][N:4]([CH3:14])[C:5]1[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[CH:7][N:6]=1.[H-].[Na+].[CH2:17](I)[CH3:18]>C1COCC1.CN(C=O)C.CCOC(C)=O>[CH2:17]([O:1][CH2:2][CH2:3][N:4]([CH3:14])[C:5]1[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[CH:7][N:6]=1)[CH3:18]

Participants

7

Reactant 3

HCID 6340IodoethaneHCID 24758Sodium hydrideHCID 1176762-(N-Methyl-N-(5-nitro-2-pyridyl)amino)ethanol

Product 1

HCID 59301393HCID 59301393, compound

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

(2-Hydroxy-ethyl)-methyl-(5-nitro-pyridin-2-yl)-amine (197 mg, 1 mmol) in THF (5 mL) and DMF (2 mL) was stirred with 60% NaH in oil (48 mg, 1.2 mmol) for 1 hr. The mixture was cooled and to this was added ethyl iodide (120 uL, 1.5 mmol). The reaction was allowed to stir overnight. The mixture was diluted with EtOAc, extracted with H2O and dried over MgSO4. The EtOAc layer was filtered, evaporated to dryness and used without further purification. Yield: 155 mg. ES-MS calcd for C10H15N3O3 (m/e) 225.25, obsd 225.1 (M+H).

Workup

  1. temperatureThe mixture was cooled
  2. extractionextracted with H2O
  3. dry with materialdried over MgSO4
  4. filtrationThe EtOAc layer was filtered
  5. customevaporated to dryness
  6. customused without further purification

Sources & evidence

ORD record
ord-717596bce4764cde973deeb7e3964ab2
Source dataset
uspto-grants-2010_05
Patent number
US07714126B2

Reaction notes

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