Sodium hydride → 6-chloro-N-[2-(propan-2-ylsulfonyl)phenyl]pyridazin-4-amine

HRID 921384Notes

Reaction equation

HRID 921384 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8]([CH:11]([CH3:13])[CH3:12])(=[O:10])=[O:9].[H-].[Na+].[Cl:16][C:17]1[N:18]=[N:19][CH:20]=[C:21](Cl)[CH:22]=1>CN(C)C=O>[Cl:16][C:17]1[N:18]=[N:19][CH:20]=[C:21]([NH:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=2[S:8]([CH:11]([CH3:13])[CH3:12])(=[O:10])=[O:9])[CH:22]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 126463662-(Propane-2-sulfonyl)anilineHCID 199596873,5-Dichloropyridazine

Product 1

HCID 866688086-chloro-N-[2-(propan-2-ylsulfonyl)phenyl]pyridazin-4-amine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 1-Amino-2-(isopropylsulphonyl)benzene (350 mg, 1.6 mmol) in 4 mL of N,N-Dimethyl formamide at 0 degree, is added Sodium hydride (100 mg) and the reaction mixture is allowed to stirred at 0 degree for 20 minutes. 3,5-dichloropyridazine (1.6 mmol) is added and the reaction mixture is warmed to room temperature. The reaction mixture is stirred at room temperature until formation of the desired compound. The reaction mixture is quenched with water and extracted with Ethyl acetate. The combined Ethyl acetate layers are dried over Sodium Sulfate and solvent is removed under reduced pressure. The residue can be purified by Prep-HPLC.

Sources & evidence

ORD record
ord-ea1d706020d042d6a78a8759a53c4429
Source dataset
uspto-grants-2016_03
Patent number
US09273077B2

Reaction notes

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