Water → N,N-Diethyl-3,6-dichloropyridazine-4-carboxamide

HRID 532353Notes

Reaction equation

HRID 532353 reaction equation
[Cl:1][C:2]1[N:3]=[N:4][C:5]([Cl:11])=[CH:6][C:7]=1[C:8](Cl)=[O:9].[CH2:12]([NH:14][CH2:15][CH3:16])[CH3:13].O>C(Cl)Cl>[CH2:12]([N:14]([CH2:15][CH3:16])[C:8]([C:7]1[CH:6]=[C:5]([Cl:11])[N:4]=[N:3][C:2]=1[Cl:1])=[O:9])[CH3:13]

Participants

5

Reactant 3

HCID 962WaterHCID 8021DiethylamineHCID 810183,6-Dichloropyridazine-4-carbonyl chloride

Product 1

HCID 58136931N,N-Diethyl-3,6-dichloropyridazine-4-carboxamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

3,6-Dichloropyridazine-4-carbonyl chloride (2.5 g) was initially charged in DCM (25 ml) at RT. Thereafter, diethylamine (1.5 ml) predissolved in DCM (5 ml) was slowly added dropwise while stirring. After stirring at RT for 3 h, the mixture was admixed with water and extracted three times with DCM. The combined DCM phases were dried over sodium sulfate, filtered and concentrated. The residue was purified by means of silica gel (70 g cartridge, n-heptane/EA gradient). 1.8 g of the title compound were obtained.

Workup

  1. additionwas slowly added dropwise
  2. stirringAfter stirring at RT for 3 h
  3. extractionextracted three times with DCM
  4. dry with materialThe combined DCM phases were dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by means of silica gel (70 g cartridge, n-heptane/EA gradient)

Sources & evidence

ORD record
ord-15ba34e5d23047ecae851d6ac8b9733e
Source dataset
uspto-grants-2014_10
Patent number
US08853206B2

Reaction notes

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