4-Methylmorpholine → N-methoxy-N-methylisoxazole-3-carboxamide

HRID 2179985Notes

Reaction equation

HRID 2179985 reaction equation
[O:1]1[CH:5]=[CH:4][C:3]([C:6]([OH:8])=O)=[N:2]1.Cl.[CH3:10][NH:11][O:12][CH3:13].CN1CCOCC1.Cl.C(N(CC)CCCN=C=NCC)C>CN(C)C1C=CN=CC=1.ClCCl>[CH3:13][O:12][N:11]([CH3:10])[C:6]([C:3]1[CH:4]=[CH:5][O:1][N:2]=1)=[O:8]

Participants

7

Reactant 4

HCID 79724-MethylmorpholineHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 99645121-(3-Diethylaminopropyl)-3-ethylcarbodiimide hydrochlorideHCID 112864533-Isoxazolecarboxylic acid

Product 1

HCID 22489102N-methoxy-N-methylisoxazole-3-carboxamideYield 63.8%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

A mixture of 3-isoxazolecarboxylic acid (4.2 g), 4-dimethylaminopyridine (5.1 g), N,O-dimethylhydroxylamine hydrochloride (4.0 g), N-methylmorpholine (4.2 g) and 1-(3-diethylaminopropyl)-3-ethylcarbodiimide hydrochloride (7.5 g) in dichloromethane (175 ml) were stirred at ambient temperature overnight. The reaction mixture was then washed with 2N hydrochloric acid (100 ml), saturated sodium bicarbonate (100 ml), brine, dried over magnesium sulphate and evaporated to give the product as a dark orange oil (3.7 g).

Workup

  1. washThe reaction mixture was then washed with 2N hydrochloric acid (100 ml), saturated sodium bicarbonate (100 ml), brine
  2. dry with materialdried over magnesium sulphate
  3. customevaporated

Sources & evidence

ORD record
ord-1680a34c180c440ca2b3d6944fa3ac67
Source dataset
uspto-grants-2005_05
Patent number
US06887871B2

Reaction notes

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