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Chlorosuccinimide → 3-Chloro-6-(chloromethyl)pyridazine

HRID 1814762
Notes
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Reaction equation

HRID 1814762 reaction equation
[Cl:1][C:2]1[N:3]=[N:4][C:5]([CH3:8])=[CH:6][CH:7]=1.[Cl:9]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>[Cl:1][C:2]1[N:3]=[N:4][C:5]([CH2:8][Cl:9])=[CH:6][CH:7]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 31398ChlorosuccinimideHCID 2272543-Chloro-6-methylpyridazine

Product 1

HCID 224986393-Chloro-6-(chloromethyl)pyridazineYield 43.9%

Reagents, catalysts & solvents 2

HCID 7187Benzoyl PeroxideCatalystHCID 5943Carbon TetrachlorideSolvent

Procedure

A suspension of 3-chloro-6-methylpyridazine (3 g), benzoyl peroxide (150 mg) and N-chlorosuccinimide (3.12 g) in CCl4 (30 ml) was refluxed 16 hours, cooled, filtered and evaporated. Chromatography (EtOAc/hexane) gave title compound (1.67 g). NMR δ(CDCl3) 4.87 (2H, s), 7.58 (1H, d), 7.71 (1H, d).

Workup

  1. temperaturewas refluxed 16 hours
  2. temperaturecooled
  3. filtrationfiltered
  4. customevaporated

Sources & evidence

ORD record
ord-9e0c875016194aaabcfe3709d8b2f394
Source dataset
uspto-grants-2005_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06878704B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes