Potassium Carbonate → 6-(5-Chloro-3-methyl-benzofuran-2-sulfenyl)-pyridazine

HRID 22729

Reaction equation

HRID 22729 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[O:9][C:8]([SH:10])=[C:7]([CH3:11])[C:6]=2[CH:12]=1.Cl[C:14]1[N:15]=[N:16][C:17](OC)=[CH:18][CH:19]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[O:9][C:8]([S:10][C:17]3[N:16]=[N:15][CH:14]=[CH:19][CH:18]=3)=[C:7]([CH3:11])[C:6]=2[CH:12]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 744033-Chloro-6-methoxypyridazineHCID 98130595-Chloro-2-mercapto-3-methyl benzofuran

Product 1

HCID 225915466-(5-Chloro-3-methyl-benzofuran-2-sulfenyl)-pyridazineYield 93%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution containing 5-chloro-2-mercapto-3-methyl benzofuran (10 mmol, 1.98 g and 3-chloro-6-methoxy pyridazine (10 mmol, 1.44 g) in dimethylformamide (DMF, 10 mL) was added potassium carbonate (20 mmol, 2.76 g) and the reaction mixture was stirred at room temperature for 3 hours. The reaction mixture was quenched with H2O (200 mL), the precipitated yellow solid was collected and the solid was purified by silica gel chromatography (eluent:hexanes:EtOAc::9:1) to obtain 6-(5-chloro-3-methyl-benzofuran-2-sulfenyl)-pyridazine (93%, 2.87 g); mp 131° C.-134° C.

Workup

  1. customThe reaction mixture was quenched with H2O (200 mL)
  2. customthe precipitated yellow solid was collected
  3. customthe solid was purified by silica gel chromatography (eluent:hexanes:EtOAc::9:1)

Sources & evidence

ORD record
ord-ef9bcfd62ad84376ab85132517bab3e4
Source dataset
uspto-grants-2005_02
Patent number
US06849629B2

Linked notes

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