Dimethylamine → HCID 22899434, compound

HRID 2234703Notes

Reaction equation

HRID 2234703 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].[CH:12]([NH:15][CH:16](C)C)(C)C.C(Cl)(=O)C(C)(C)C.CNC>ClCCl>[CH3:12][N: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]

Participants

6

Reactant 4

HCID 674DimethylamineHCID 7912DiisopropylamineHCID 62493Pivaloyl chlorideHCID 4338043,6-Dichloropyridazine-4-carboxylic acid

Product 1

HCID 22899434HCID 22899434, compoundYield 62.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3,6-Dichloro-pyridazine-4-carboxylic acid (500 mg, 2.59 mmol) was dissolved in dichloromethane (2 mL), treated with di-iso-propylamine (454 μL, 2.59 mmol) and cooled in an ice water bath. Pivaloyl chloride (318 μL, 2.59 mmol) was added and the mixture was stirred for 25 minutes. 2 M dimethylamine (2.59 mL, 5.18 mmol) was added and the reaction was stirred 15 h. The mixture was washed with saturated ammonium chloride (1×), saturated sodium bicarbonate (1×), and dried over sodium sulfate to afford 3,6-dichloro-pyridazine-4-carboxylic acid dimethylamide (353 mg, 62.2%). MS: m/z 220 (M+H+).

Workup

  1. temperaturecooled in an ice water bath
  2. stirringthe reaction was stirred 15 h
  3. washThe mixture was washed with saturated ammonium chloride (1×), saturated sodium bicarbonate (1×)
  4. dry with materialdried over sodium sulfate

Sources & evidence

ORD record
ord-22462bac461042a8b7e195a73629ea23
Source dataset
uspto-grants-2010_05
Patent number
US07709645B2

Reaction notes

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