Diethyl Sulfate → HCID 66628133, compound

HRID 1970718Notes

Reaction equation

HRID 1970718 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH2:7][NH:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][N:10]=1.[H-].[Na+].S(OCC)(O[CH2:21][CH3:22])(=O)=O>CN(C)C=O>[CH2:21]([N:8]([CH2:7][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][N:10]=1)[CH3:22]

Participants

5

Reactant 3

HCID 6163Diethyl SulfateHCID 24758Sodium hydrideHCID 12221910HCID 12221910, compound

Product 1

HCID 66628133HCID 66628133, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a flask were added 2.5 g N-(pyridin-2-ylmethyl)pyridin-2-amine and 40 ml N,N-dimethylformamide, and the mixture was cooled to 5 C. To this mixture was added 0.65 g of 60% sodium hydride in mineral oil in small portions, and after stirring at 5-10 C for ten minutes, 2.2 g of diethyl sulfate were added. The reaction mixture was heated to 45 C for 16 hours, then cooled to 22 C and quenched with 40 ml water. The product was extracted twice with 40 ml hexane and following removal of the solvent, the product was purified by silica gel chromatography using a gradient from 50% ethyl acetate, 49% hexane and 1% methanol to 60% ethyl acetate, 39% hexane, and 1% methanol resulting in 1.4 g of a yellow oil.

Workup

  1. temperaturethe mixture was cooled to 5 C
  2. temperatureThe reaction mixture was heated to 45 C for 16 hours
  3. temperaturecooled to 22 C
  4. customquenched with 40 ml water
  5. extractionThe product was extracted twice with 40 ml hexane
  6. customremoval of the solvent
  7. customthe product was purified by silica gel chromatography

Sources & evidence

ORD record
ord-8a838cef78b44525abec7a9cae1eed2b
Source dataset
uspto-grants-2013_04
Patent number
US08431045B2

Reaction notes

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