HomeMCPWorkbenchSkills
HomeWorkbenchNotificationsMe
llms.txt · MCP GuidePrivacy Policy · Terms of Service · Supportv1.8.0
  1. Home
  2. /Reaction

Sodium Chloride → (4-Chloro-2-fluorophenyl)(6-chloro-2-methylimidazo[1,2-b]pyridazin-3-yl)methanone

HRID 597856
Notes
Print preview

Reaction equation

HRID 597856 reaction equation
[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
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 4

HCID 5234Sodium ChlorideHCID 24083Sulfuric acid magnesium salt (1:1)HCID 450810122-Chloro-1-(4-chloro-2-fluorophenyl)ethan-1-oneHCID 178463304HCID 178463304, compound

Product 1

HCID 56954583(4-Chloro-2-fluorophenyl)(6-chloro-2-methylimidazo[1,2-b]pyridazin-3-yl)methanoneYield 57%

Reagents, catalysts & solvents 3

HCID 962WaterSolvent2×HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
120 °C

Procedure

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).

Workup

  1. customIn a round bottom flask combine
  2. temperatureLet cool to RT
  3. filtrationFilter
  4. concentrationconcentrate in vacuo
  5. customPurify by silica plug (hexane→4:1 hexane

Sources & evidence

ORD record
ord-8a133918b155450c86a4f24fad571d22
Source dataset
uspto-grants-2011_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07897600B2

Reaction notes

Loading…

On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes