Sodium Carbonate → 6-(2,4-Dimethylphenyl)pyridazine-3-thiol

HRID 868744Notes

Reaction equation

HRID 868744 reaction equation
Cl[C:2]1[N:3]=[N:4][C:5]([C:8]2[CH:13]=[CH:12][C:11]([CH3:14])=[CH:10][C:9]=2[CH3:15])=[CH:6][CH:7]=1.NC(N)=[S:18].C([O-])([O-])=O.[Na+].[Na+]>CCO>[CH3:15][C:9]1[CH:10]=[C:11]([CH3:14])[CH:12]=[CH:13][C:8]=1[C:5]1[CH:6]=[CH:7][C:2](=[S:18])[NH:3][N:4]=1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 2723790ThioureaHCID 123687643-Chloro-6-(2,4-dimethylphenyl)pyridazine

Product 1

HCID 125621006-(2,4-Dimethylphenyl)pyridazine-3-thiolYield 83.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

3-chloro-6-(2,4-dimethylphenyl)pyridazine (example 13b) (1.36 g) was refluxed with thiourea (473 mg, 6.2 mmol) in EtOH (25 mL) for 5 hrs. The mixture was evaporated, and water (45 mL) was added to the residue, followed by Na2CO3 (318 mg, 3 mmol). The precipitate that formed was collected by filtration, washed with diethylether and dried to give 6-(2,4-Dimethylphenyl)pyridazine-3(2H)-thione (1.12 g, 52%). 1H NMR (300 MHz, dMSO): δ 2.29 (s, 3H), 2.32 (s, 3H), 7.12-7.30 (m, 2H), 7.29-7.31 (d, 1H), 7.46-7.49 (d, 1H), 7.65-7.68 (dd, 1H); MS (M+H, 217).

Workup

  1. customThe mixture was evaporated
  2. additionwater (45 mL) was added to the residue
  3. customThe precipitate that formed
  4. filtrationwas collected by filtration
  5. washwashed with diethylether
  6. customdried

Sources & evidence

ORD record
ord-921e90b7b806411aa18f29e0697c784b
Source dataset
uspto-grants-2015_03
Patent number
US08968708B2

Reaction notes

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