Water → N1-Benzyl-N2-(6-chloro-4,5-dimethylpyridazin-3-yl)ethane-1,2-diamine

HRID 2093361Notes

Reaction equation

HRID 2093361 reaction equation
[Cl:1][C:2]1[N:3]=[N:4][C:5](Cl)=[C:6]([CH3:9])[C:7]=1[CH3:8].[CH2:11]([NH:18][CH2:19][CH2:20][NH2:21])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C(N(C(C)C)CC)(C)C.O>CS(C)=O>[CH2:11]([NH:18][CH2:19][CH2:20][NH:21][C:5]1[N:4]=[N:3][C:2]([Cl:1])=[C:7]([CH3:8])[C:6]=1[CH3:9])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

6

Reactant 4

HCID 962WaterHCID 77801N-BenzylethylenediamineHCID 81531DiisopropylethylamineHCID 211875053,6-Dichloro-4,5-dimethylpyridazine

Product 1

HCID 86655911N1-Benzyl-N2-(6-chloro-4,5-dimethylpyridazin-3-yl)ethane-1,2-diamine

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

Heat a mixture of 3,6-dichloro-4,5-dimethylpyridazine (6.90 g, 39.0 mmol), N-benzylethylenediamine (8.78 g, 58.5 mmol), and diisopropylethylamine (25.2 g, 195 mmol) in DMSO (78 mL) at 120° C. for 3 d. Cool the reaction mixture, pour into H2O, and extract the mixture with Et2O. Wash the organic layer with H2O, dry over Na2SO4, filter, and concentrate under reduced pressure. Purify the residue using flash silica gel chromatography (gradient of 0 to 5% 2 M NH3/MeOH in CH2Cl2) to obtain the title compound as a waxy solid (6.41 g, 57%). ES/MS m/z 291.2 (M+1).

Workup

  1. temperatureHeat
  2. temperatureCool the reaction mixture
  3. extractionextract the mixture with Et2O
  4. washWash the organic layer with H2O
  5. dry with materialdry over Na2SO4
  6. filtrationfilter
  7. concentrationconcentrate under reduced pressure
  8. customPurify the residue

Sources & evidence

ORD record
ord-66af781fdcc84ea4a071ab1063a6dc9f
Source dataset
uspto-grants-2013_05
Patent number
US08445493B2

Reaction notes

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