6-Amino-3-chloropyridazine → HCID 178463304, compound

HRID 597865Notes

Reaction equation

HRID 597865 reaction equation
[Cl:1][C:2]1[N:7]=[N:6][C:5]([NH2:8])=[CH:4][CH:3]=1.CO[C:11](OC)([N:13]([CH3:15])[CH3:14])[CH3:12].COC1CCCC1>>[Cl:1][C:2]1[N:7]=[N:6][C:5](/[N:8]=[C:11](/[N:13]([CH3:15])[CH3:14])\[CH3:12])=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 216436-Amino-3-chloropyridazineHCID 878351,1-Dimethoxyethyl(dimethyl)amineHCID 138539Cyclopentyl methyl ether

Product 1

HCID 178463304HCID 178463304, compound

Procedure

Combine 6-chloropyridazin-3-amine (1.500 kg, 11.58 mol); 1,1-dimethoxy-N,N-dimethylethanamine (2.313 kg, 17.37 mol) and cyclopentyl methyl ether (8.25 L) then heat to 98° C. while distilling off the resulting methanol byproduct. After 4 h, the reaction mixture is cooled to ambient temperature and heptanes (11.2 L) is added to the reaction solution for crystallizing the product. The title compound is collected by filtration and is dried. (1.494 kg, 64.95%; mp=73° C.)

Workup

  1. distillationwhile distilling off the resulting methanol byproduct
  2. additionheptanes (11.2 L) is added to the reaction solution
  3. customfor crystallizing the product
  4. filtrationThe title compound is collected by filtration
  5. customis dried

Sources & evidence

ORD record
ord-cc25a493e9be43f5bf9b19c923cba491
Source dataset
uspto-grants-2011_03
Patent number
US07897600B2

Reaction notes

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