[Cl:1][C:2]1[N:7]=[N:6][C:5](/[N:8]=[C:9](/N(C)C)\[CH3:10])=[CH:4][CH:3]=1.Cl[CH2:15][C:16]([C:18]1[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][C:19]=1[F:25])=[O:17].[Cl-].[Na+].S([O-])([O-])(=O)=O.[Mg+2]>CC(=O)OCC.O.CN(C)C=O>[Cl:24][C:21]1[CH:22]=[CH:23][C:18]([C:16]([C:15]2[N:6]3[N:7]=[C:2]([Cl:1])[CH:3]=[CH:4][C:5]3=[N:8][C:9]=2[CH3:10])=[O:17])=[C:19]([F:25])[CH:20]=1
In a round bottom flask combine (E)-N′-(6-chloropyridazin-3-yl)-N,N-dimethylacetimidamide (36.61 g, 184.3 mmol), 2-chloro-1-(4-chloro-2-fluorophenyl)ethanone (38.15 g, 1 equiv.), and dimethylformamide (150 mL). Place under nitrogen then heat at 120° C. for 4 h. Let cool to RT and stir overnight. Dilute with EA (1 L) and water (500 mL). Extract organics three times with water followed by aqueous saturated sodium chloride aqueous. Dry organics over anhydrous magnesium sulfate. Filter and concentrate in vacuo. Purify by silica plug (hexane→4:1 hexane:EA→3:1 hexane:EA→2:1 hexane:EA→1:1 hexane:EA) and isolate the title compound (33.8 g, 57%) as a light green solid. LCMS (4 min=324.0, 326.0, M+1).
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