Sulfuric Acid → HCID 12218643, compound

HRID 1836185Notes

Reaction equation

HRID 1836185 reaction equation
[C:1]1([CH2:11][C:12]#N)[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.[CH3:14]I.[H-].[Na+].OS(O)(=O)=O.C[N:24]([CH:26]=O)C>C(OCC)(=O)C>[CH3:14][C:11]([C:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1)([CH3:12])[C:26]#[N:24]

Participants

7

Reactant 5

HCID 1118Sulfuric AcidHCID 6228DimethylformamideHCID 6328Methyl iodideHCID 85961-NaphthaleneacetonitrileHCID 24758Sodium hydride

Product 1

HCID 12218643HCID 12218643, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
25 °C

Procedure

A solution of 16.7 g (100 mmol) of 1-naphthylacetonitrile in 200 m of DMF and 15 ml (240 mmol) of methyl iodide is mixed at 0° C. with 10.4 g (260 mmol) of sodium hydride (addition within 2.5 hours). The batch is stirred for 3 hours at 0° C. and for 18 hours at 25° C. It is mixed with ice and ethyl acetate. The organic phase is acidified with 10% H2SO4, washed three times with water, dried (Na2SO4) and concentrated by evaporation in a vacuum. A large-scale purification is carried out by bulb tube distillation (boiling range 60-130° C.) in an oil pump vacuum; yield: 18.8 g.

Workup

  1. washwashed three times with water
  2. dry with materialdried (Na2SO4)
  3. concentrationconcentrated by evaporation in a vacuum
  4. customA large-scale purification
  5. customis carried out by bulb tube
  6. distillationdistillation (boiling range 60-130° C.) in an oil pump vacuum

Sources & evidence

ORD record
ord-cd9c9ee52c374c88a46a2f5ca4f52058
Source dataset
uspto-grants-2004_08
Patent number
US06777409B2

Reaction notes

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