4-Toluenesulfonyl chloride → 2-Tosyl-2,3-dihydropyridazine-3-carbonitrile

HRID 2203345Notes

Reaction equation

HRID 2203345 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][N:2]=1.C[Si]([C:11]#[N:12])(C)C.[Cl-].[Al+3].[Cl-].[Cl-].[C:17]1([CH3:27])[CH:22]=[CH:21][C:20]([S:23](Cl)(=[O:25])=[O:24])=[CH:19][CH:18]=1>C(Cl)Cl.CCO>[CH3:27][C:17]1[CH:22]=[CH:21][C:20]([S:23]([N:1]2[CH:6]([C:11]#[N:12])[CH:5]=[CH:4][CH:3]=[N:2]2)(=[O:25])=[O:24])=[CH:19][CH:18]=1

Participants

7

Reactant 4

HCID 73974-Toluenesulfonyl chlorideHCID 9259PyridazineHCID 82115Trimethylsilyl cyanideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 136429372-Tosyl-2,3-dihydropyridazine-3-carbonitrile

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of pyridazine (3.63 mL, 49.9 mmol) in DCM (60 mL) was added trimethylsilyl cyanide (11.99 mL, 90 mmol) and aluminum chloride (20 mg, 0.150 mmol). After stirring the reaction mixture at room temperature for 10 minutes, a solution of para-toluene sulfonyl chloride (16.38 mL, 86 mmol) in DCM (100 mL) was added dropwise via an addition funnel over 30 minutes. The resulting light orange solution was left stirring at room temperature overnight. The reaction mixture was concentrated to give a light brown solid. To this material was added EtOH (100 mL). A white precipitate formed which was filtered through a sintered funnel. The precipitate was washed with ethanol and collected. m/z=262 (M+H).

Workup

  1. waitThe resulting light orange solution was left
  2. stirringstirring at room temperature overnight
  3. concentrationThe reaction mixture was concentrated
  4. customto give a light brown solid
  5. customA white precipitate formed which
  6. filtrationwas filtered through a sintered funnel
  7. washThe precipitate was washed with ethanol
  8. customcollected

Sources & evidence

ORD record
ord-2cf5397323b9446ab28ca5493934a527
Source dataset
uspto-grants-2016_06
Patent number
US09365574B2

Reaction notes

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