Sodium hydride → 4-(6-Chloro-3-pyridazinyloxy)-2,5-dimethylbenzeneamine

Reaction equation

[H-].[Na+].[Cl:3][C:4]1[N:5]=[N:6][C:7](Cl)=[CH:8][CH:9]=1.[NH2:11][C:12]1[C:17]([CH3:18])=[CH:16][C:15]([OH:19])=[C:14]([CH3:20])[CH:13]=1>CS(C)=O>[Cl:3][C:4]1[N:5]=[N:6][C:7]([O:19][C:15]2[C:14]([CH3:20])=[CH:13][C:12]([NH2:11])=[C:17]([CH3:18])[CH:16]=2)=[CH:8][CH:9]=1

Participants

Procedure

4.8 g of sodium hydride was added in portions to a stirred solution of 30 g of 3,6-dichloropyridazine and 27.4 g of 4-amino-2,5-dimethylphenol in 300 ml of dimethyl sulfoxide. The temperature of the mixture rose to 65° C. The mixture was then stirred for 18 hours at room temperature, poured over ice water and filtered. Recrystallization of the filter cake from methanol gave 4-(6-chloro-3-pyridazinyloxy)-2,5-dimethylbenzeneamine, as a brown solid (5A), mp: 138°-140° C.