Hydrochloric Acid → N-methoxy-N-methylisoxazole-5-carboxamide

HRID 2179963Notes

Reaction equation

HRID 2179963 reaction equation
[O:1]1[C:5]([C:6]([OH:8])=O)=[CH:4][CH:3]=[N:2]1.Cl.[CH3:10][O:11][NH:12][CH3:13].CCN=C=NCCCN(C)C.CN(C1C=CC=CN=1)C.CN1CCOCC1.Cl>ClCCl>[CH3:10][O:11][N:12]([CH3:13])[C:6]([C:5]1[O:1][N:2]=[CH:3][CH:4]=1)=[O:8]

Participants

8

Reactant 6

HCID 313Hydrochloric AcidHCID 79724-MethylmorpholineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 218852-DimethylaminopyridineHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 20605991,2-Oxazole-5-carboxylic acid

Product 1

HCID 22489934N-methoxy-N-methylisoxazole-5-carboxamideYield 76%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of isoxazole 5-carboxylic acid (2.81 g), N-methoxy-N-methylamine hydrochloride (2.49 g), EDCI (4.96 g), dimethylaminopyridine (3.15 g) and 4-methylmorpholine (2.8 ml) in dichloromethane (20 ml) was stirred for 18 h. 2M Hydrochloric acid was added and the mixture was extracted with dichloromethane (three times). The organic layers were washed with aqueous sodium hydrogen carbonate and then brine, combined, dried (magnesium sulphate), evaporated and purified by chromatography on silica eluting with petrol-ether to give the sub-title compound as a colourless oil (2.94 g, 76%).

Workup

  1. extractionthe mixture was extracted with dichloromethane (three times)
  2. washThe organic layers were washed with aqueous sodium hydrogen carbonate
  3. dry with materialdried (magnesium sulphate)
  4. customevaporated
  5. custompurified by chromatography on silica eluting with petrol-ether

Sources & evidence

ORD record
ord-25336c835b3447b7b482c43cb98ad6c6
Source dataset
uspto-grants-2005_05
Patent number
US06887871B2

Reaction notes

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