2-Chloronicotinonitrile → HCID 18947911, compound

HRID 1769444Notes

Reaction equation

HRID 1769444 reaction equation
[CH3:1][N:2](S(C1C=CC=CC=1)(=O)=O)[N:3]=[C:4](Cl)[C:5]1[C:10]([Cl:11])=[CH:9][CH:8]=[CH:7][C:6]=1[Cl:12].[Cl:23][C:24]1[C:29]([C:30]#[N:31])=[CH:28][CH:27]=[CH:26][N:25]=1.[Cl-].[Al+3].[Cl-].[Cl-]>C1C(Cl)=CC=C(Cl)C=1>[Cl:11][C:10]1[CH:9]=[CH:8][CH:7]=[C:6]([Cl:12])[C:5]=1[C:4]1[N:31]=[C:30]([C:29]2[C:24]([Cl:23])=[N:25][CH:26]=[CH:27][CH:28]=2)[N:2]([CH3:1])[N:3]=1

Participants

5

Reactant 3

HCID 810792-ChloronicotinonitrileHCID 6451240Aluminum(III) ChlorideHCID 54261612HCID 54261612, compound

Product 1

HCID 18947911HCID 18947911, compoundYield 37.3%

Reagents, catalysts & solvents 1

HCID 46851,4-DichlorobenzeneSolvent

Procedure

In 50 ml of dichlorobenzene were dissolved 5.7 g of N-methyl-N-phenylsulfonyl-2,6-dichloro-benzohydrazonoyl chloride and 2.3 g of 2-chloro-3-cyanopyridine, to which was added 2.2 g of anhydrous aluminum chloride at room temperature with stirring. The resulting solution was raised to 120°-140° C. in an oil bath and stirred for 4 hours. After the completion of the reaction, the reaction solution was washed with a diluted alkali solution and further with a diluted hydrochloric acid solution. After the washing with water, the organic layer was dried over anhydrous magnesium sulfate and concentrated under a reduced pressure. The resulting concentrate was subjected to a chromatography of silica gel (trade mark: Wakogel C-200) using a mixed solution of hexane and ethyl acetate as a developing solvent to obtain 1.9 g (yield: 37.3%) of a desired light brown granular crystal (melting point: 133.0°-135.5° C.).

Workup

  1. temperatureThe resulting solution was raised to 120°-140° C. in an oil bath
  2. stirringstirred for 4 hours
  3. customAfter the completion of the reaction
  4. washthe reaction solution was washed with a diluted alkali solution and further with a diluted hydrochloric acid solution
  5. dry with materialAfter the washing with water, the organic layer was dried over anhydrous magnesium sulfate
  6. concentrationconcentrated under a reduced pressure
  7. concentrationThe resulting concentrate

Sources & evidence

ORD record
ord-262785b3794446c29d3cfcb8c0170740
Source dataset
uspto-grants-1995_01
Patent number
US05380944

Reaction notes

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