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

HRID 1472048Notes

Reaction equation

HRID 1472048 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-1c2b096732ef42d7a0d48ccadc4d5baa
Source dataset
uspto-grants-2015_04
Patent number
US09012462B2

Reaction notes

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