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

HRID 1525307Notes

Reaction equation

HRID 1525307 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][N:2]=1.[Cl-].[Al+3].[Cl-].[Cl-].[Si]([C:15]#[N:16])(C)(C)C.[S:17](Cl)([C:20]1[CH:26]=[CH:25][C:23]([CH3:24])=[CH:22][CH:21]=1)(=[O:19])=[O:18]>C(Cl)Cl>[S:17]([N:1]1[CH:6]([C:15]#[N:16])[CH:5]=[CH:4][CH:3]=[N:2]1)([C:20]1[CH:26]=[CH:25][C:23]([CH3:24])=[CH:22][CH:21]=1)(=[O:19])=[O:18]

Participants

6

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 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of pyridazine, 30-ia, (5 mL, 69.12 mmol), aluminum chloride (28 mg, 0.21 mmol) and TMSCN (16.75 mmol) in DCM (60 mL) was stirred under a nitrogen atmosphere at 0° C. for 20 min. A solution of TsCl (22.75 g, 119.7 mmol) in DCM (40 mL) was added dropwise. The reaction was warmed to room temperature, stirred for an additional 60 h, and concentrated in vacuo. The residue was washed with EtOH (150 mL) and the resulting solids were filtered to afford the title compound, 30-ib, (15 g, 83%). 1H NMR (300 MHz, CDCl3) δ7.93 (d, J=8.4 Hz, 2H), 7.38 (d, J=1.8 Hz, 2H), 6.23-6.21 (m, 2H), 5.79 (d, J=6.3 Hz, 1H), 2.44 (s, 3H). LC-MS: (M+H)+ 262.

Workup

  1. concentrationconcentrated in vacuo
  2. washThe residue was washed with EtOH (150 mL)
  3. filtrationthe resulting solids were filtered

Sources & evidence

ORD record
ord-133ac37554a54b4c9ffc13c3a6d25845
Source dataset
uspto-grants-2015_07
Patent number
US09079930B2

Reaction notes

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