Pyridine → HCID 51109753, compound

HRID 633698

Reaction equation

HRID 633698 reaction equation
N1C=CC=CC=1.Cl.[CH3:8][NH:9][O:10][CH3:11].[CH3:12][C:13]1[C:17]([C:18](Cl)=[O:19])=[C:16]([CH3:21])[O:15][N:14]=1>ClCCl.C([O-])(O)=O.[Na+].C1(C)C=CC=CC=1>[CH3:11][O:10][N:9]([CH3:8])[C:18]([C:17]1[C:13]([CH3:12])=[N:14][O:15][C:16]=1[CH3:21])=[O:19]

Participants

7

Reactant 3

HCID 1049PyridineHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 27362653,5-Dimethylisoxazole-4-carbonyl Chloride

Product 1

HCID 51109753HCID 51109753, compoundYield 98.9%

Reagents, catalysts & solvents 3

HCID 1140TolueneSolventHCID 6344DichloromethaneSolvent2×HCID 516892Sodium BicarbonateSolvent

Procedure

659 μl (8.15 mmol) of pyridine are added to a suspension of 343.07 mg (3.45 mmol) of N,O-dimethylhydroxylamine hydrochloride in 10 mL of dichloromethane. The mixture is stirred at room temperature until fully dissolved. A solution of 526.32 mg (3.13 mmol) of 3,5-dimethylisoxazole-4-carbonyl chloride in 5 mL of dichloromethane is then added. After stirring for 1 hour at room temperature, the reaction mixture is taken up in saturated aqueous NaHCO3 solution and stirred for a few minutes, and the phases are separated by settling. The organic phase is dried over magnesium sulfate and evaporated to dryness. The residue obtained is taken up in toluene and evaporated, the operation being repeated a second time. 570 mg of N-methoxy-N-methyl-3,5-dimethylisoxazole-4-carboxamide are then obtained, corresponding to the following characteristics:

Workup

  1. dissolutionuntil fully dissolved
  2. stirringAfter stirring for 1 hour at room temperature
  3. stirringstirred for a few minutes
  4. customthe phases are separated
  5. dry with materialThe organic phase is dried over magnesium sulfate
  6. customevaporated to dryness
  7. customThe residue obtained
  8. customevaporated

Sources & evidence

ORD record
ord-31d42ef2e01f42079414ff88fdf1d682
Source dataset
uspto-grants-2016_04
Patent number
US09321790B2

Linked notes

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