1,2-Dichloroethane → HCID 22310829, compound

HRID 227587Notes

Reaction equation

HRID 227587 reaction equation
CO[C:3]1[CH:8]=[C:7]([N+:9]([O-:11])=[O:10])[CH:6]=[CH:5][N:4]=1.S([O-])([O:15][CH3:16])(=O)=O.ClCCCl.[C-:22]#[N:23].[Na+]>O>[C:22]([C:3]1[C:8]([O:15][CH3:16])=[C:7]([N+:9]([O-:11])=[O:10])[CH:6]=[CH:5][N:4]=1)#[N:23]

Participants

6

Reactant 4

HCID 111,2-DichloroethaneHCID 8929Sodium CyanideHCID 4694097Methyl sulfate(1-)HCID 540631072-Methoxy-4-nitropyridine

Product 1

HCID 22310829HCID 22310829, compoundYield 53%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of 12.5 g (12.5 moles) of the N-oxide of 3 methoxy-4-nitropyridine, 7.72 ml (1.1 eq.) of methyl sulfate and 70 ml of 1,2-dichloroethane is heated at 70° C. for 2.5 hours. It is allowed to cool and 70 ml of water are added. It is cooled in a salt and ice bath and, in portions, 7.55 g (2.1 moles) of sodium cyanide are added, controlling the temperature so as not to exceed 10° C. After 4 hours stirring, the reaction mixture is extracted with ethyl ether, the organic phase is washed with water, concentrated and the residue chromatographed (ethyl acetate/dichloromethane). There is obtained 7.06 g of a yellow oil (yield 53%).

Workup

  1. temperatureto cool
  2. additionare added
  3. customto exceed 10° C
  4. extractionthe reaction mixture is extracted with ethyl ether
  5. washthe organic phase is washed with water
  6. concentrationconcentrated
  7. customthe residue chromatographed (ethyl acetate/dichloromethane)

Sources & evidence

ORD record
ord-0d05d36819924c659196ec8e8a75781e
Source dataset
uspto-grants-2009_07
Patent number
US07560565B2

Reaction notes

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