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

HRID 217703Notes

Reaction equation

HRID 217703 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-39f4a29bdcde4c9d948a9e07ae7138b0
Source dataset
uspto-grants-2012_06
Patent number
US08198272B2

Reaction notes

Loading…