Thionyl Chloride → 3,6-Dichloropyridazine-4-carbonyl chloride

HRID 1685062Notes

Reaction equation

HRID 1685062 reaction equation
[Cl:1][C:2]1[N:3]=[N:4][C:5]([Cl:11])=[CH:6][C:7]=1[C:8](O)=[O:9].O=S(Cl)[Cl:14]>C1(C)C=CC=CC=1.CN(C=O)C>[Cl:1][C:2]1[N:3]=[N:4][C:5]([Cl:11])=[CH:6][C:7]=1[C:8]([Cl:14])=[O:9]

Participants

5

Reactant 2

HCID 24386Thionyl ChlorideHCID 4338043,6-Dichloropyridazine-4-carboxylic acid

Product 1

HCID 810183,6-Dichloropyridazine-4-carbonyl chloride

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 1140TolueneSolvent

Procedure

To a suspension of 3,6-dichloropyridazine-4-carboxylic acid (1.16 g, 6 mmol) in toluene (20 mL) were added DMF (2 drops) and SOCl2 (4 mL) and the mixture was heated at reflux temperature for 3 h. The volatiles were removed and the residue was stripped with toluene. The resulting brown oil (3,6-dichloropyridazine-4-carbonyl chloride) was used without purification.

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux temperature for 3 h
  3. customThe volatiles were removed
  4. customThe resulting brown oil (3,6-dichloropyridazine-4-carbonyl chloride) was used without purification

Sources & evidence

ORD record
ord-b09902e606814bf5bdbf50f9eb90975c
Source dataset
uspto-grants-2012_04
Patent number
US08148380B2

Reaction notes

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