Dimethylamine → HCID 86666889, compound

HRID 510974Notes

Reaction equation

HRID 510974 reaction equation
[Cl:1][C:2]1[N:7]=[N:6][CH:5]=[C:4]([C:8](Cl)=[O:9])[CH:3]=1.[CH3:11][NH:12][CH3:13]>C(Cl)Cl.C1COCC1>[Cl:1][C:2]1[N:7]=[N:6][CH:5]=[C:4]([C:8]([N:12]([CH3:13])[CH3:11])=[O:9])[CH:3]=1

Participants

5

Reactant 2

HCID 674DimethylamineHCID 86666890HCID 86666890, compound

Product 1

HCID 86666889HCID 86666889, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

The 6-chloropyridazine-4-carbonyl chloride (0.18 g, 1.04 mmol was dissolved in methylene chloride (12.0 mL) and a 2.0 M dimethylamine in THF (1.4 mL) was added at room temperature. The reaction was stirred for 1 h and was complete. The reaction was partitioned between EtOAc and water. The organic layer was washed with 1 N HCl, brine, dried over magnesium sulfate and concentrated to give the crude product as an amber oil. The product was purified by chromatography on silica gel eluting with hexane:EtOAc gradient to give 6-chloro-N,N-dimethylpyridazine-4-carboxamide as a colorless viscous oil, (0.16 gm, 60%). LCMS calculated for C7H9ClN3O (M+H)+: m/z=186.0. found: 185.9.

Workup

  1. customThe reaction was partitioned between EtOAc and water
  2. washThe organic layer was washed with 1 N HCl, brine
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated
  5. customto give the crude product as an amber oil
  6. customThe product was purified by chromatography on silica gel eluting with hexane

Sources & evidence

ORD record
ord-095955d35eea4077a1061114bc4396ec
Source dataset
uspto-grants-2015_08
Patent number
US09096600B2

Reaction notes

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