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

HRID 597855Notes

Reaction equation

HRID 597855 reaction equation
[Cl:1][C:2]1[N:3]=[N:4][C:5]([NH2:8])=[CH:6][CH:7]=1.CO[C:11](OC)([N:13]([CH3:15])[CH3:14])[CH3:12]>C1(C)C=CC=CC=1>[Cl:1][C:2]1[N:3]=[N:4][C:5](/[N:8]=[C:11](/[N:13]([CH3:15])[CH3:14])\[CH3:12])=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 216436-Amino-3-chloropyridazineHCID 878351,1-Dimethoxyethyl(dimethyl)amine

Product 1

HCID 178463304HCID 178463304, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

In a 2 L round bottom flask combine 3-chloro-6-pyridazinamine (43.2 g, 333.5 mmol), toluene (500 mL), and N,N-dimethylacetamide dimethyl acetal (67.8 mL, 1.25 equiv.). Attach a reflux condenser then heat to reflux for 2 h. Let cool to RT. Concentrate in vacuo. Triturate the crude material with hexanes and filter to isolate the title compound (60.4 g, 91%) as a light tan solid. MS=199.0 (M+1).

Workup

  1. customIn a 2 L round bottom flask combine
  2. temperaturethen heat
  3. temperatureto reflux for 2 h
  4. concentrationConcentrate in vacuo
  5. customTriturate the crude material with hexanes
  6. filtrationfilter

Sources & evidence

ORD record
ord-8f2a5146bbc848b49a8899ce14f93f3c
Source dataset
uspto-grants-2011_03
Patent number
US07897600B2

Reaction notes

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