6-Amino-3-chloropyridazine → HCID 178484245, compound

HRID 1513780Notes

Reaction equation

HRID 1513780 reaction equation
[Cl:1][C:2]1[N:7]=[N:6][C:5]([NH2:8])=[CH:4][CH:3]=1.CO[CH:11](OC)[N:12]([CH3:14])[CH3:13]>>[Cl:1][C:2]1[N:7]=[N:6][C:5](/[N:8]=[CH:11]/[N:12]([CH3:14])[CH3:13])=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 216436-Amino-3-chloropyridazineHCID 78373Dimethylformamide dimethyl acetal

Product 1

HCID 178484245HCID 178484245, compoundYield 82.9%

Conditions

Temperature
110 °C

Procedure

A 500 mL RB flask was charged with 6-chloropyridazin-3-amine (10.0 g, 77.2 mmol) and dimethoxy-N,N-dimethylmethanamine (206 ml, 1544 mmol), equipped with a reflux condenser, then heated to 110° C. for 3 hours then left at room temperature for 16 hours. The precipitate was collected by filtration. The mother liquor was concentrated down to give an yellow solid, which was triturated with EtOAc and collected. The solids were combined to give (E)-N′-(6-chloropyridazin-3-yl)-N,N-dimethylformamidine (11.81 g, 82.9% yield) as a white solid

Workup

  1. customequipped with a reflux condenser
  2. filtrationThe precipitate was collected by filtration
  3. concentrationThe mother liquor was concentrated down
  4. customto give an yellow solid, which
  5. customwas triturated with EtOAc
  6. customcollected

Sources & evidence

ORD record
ord-07b6984eca254186925114ed1246ea39
Source dataset
uspto-grants-2012_07
Patent number
US08217177B2

Reaction notes

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