Dimethyl Sulfate → HCID 20375992, compound

HRID 1448846Notes

Reaction equation

HRID 1448846 reaction equation
[Cl:1][C:2]1[CH:15]=[CH:14][CH:13]=[CH:12][C:3]=1[O:4][C:5]1[CH:6]=[N+:7]([O-])[CH:8]=[CH:9][CH:10]=1.COS(OC)(=O)=O.ClC1C=CC=CC=1OC1[CH:28]=[N+:29](OC)C=CC=1.[C-]#N.[Na+]>O>[Cl:1][C:2]1[CH:15]=[CH:14][CH:13]=[CH:12][C:3]=1[O:4][C:5]1[C:6]([C:28]#[N:29])=[N:7][CH:8]=[CH:9][CH:10]=1

Participants

6

Reactant 4

HCID 6497Dimethyl SulfateHCID 8929Sodium CyanideHCID 20375999HCID 20375999, compoundHCID 20376001HCID 20376001, compound

Product 1

HCID 20375992HCID 20375992, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 22 g of 3-(2-chlorophenoxy)pyridine 1-oxide and 22 g of dimethylsulfate is heated at 100° C. for 4 hours. The 3-(2-chlorophenoxy)-1-methoxypyridinium methosulfate is cooled and dissolved in 100 ml of water. This solution is added dropwise with stirring to a 0°-5° C. solution of 50 g of sodium cyanide in 100 ml under a nitrogen atmosphere. The mixture is stirred 16 hours and extracted with 250 ml of chloroform. The extract is dried, concentrated and distilled to yield 3-(2-chlorophenoxy)-2-pyridine-carbonitrile, bp 125°-135° C. at 01. mM, mp 90°-92° C. after recrystallization from isopropanol.

Workup

  1. additionThis solution is added dropwise
  2. extractionextracted with 250 ml of chloroform
  3. customThe extract is dried
  4. concentrationconcentrated
  5. distillationdistilled

Sources & evidence

ORD record
ord-54cfb6b6010649b2aeff112d9bc700f9
Source dataset
uspto-grants-1980_02
Patent number
US04187379

Reaction notes

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