Pyridine → N-Methoxy-N,4-dimethyloxazole-5-carboxamide

HRID 975035

Reaction equation

HRID 975035 reaction equation
[CH3:1][C:2]1[N:3]=[CH:4][O:5][C:6]=1[C:7](Cl)=[O:8].Cl.[CH3:11][NH:12][O:13][CH3:14].N1C=CC=CC=1.C(=O)([O-])O.[Na+]>C(Cl)(Cl)Cl>[CH3:14][O:13][N:12]([CH3:11])[C:7]([C:6]1[O:5][CH:4]=[N:3][C:2]=1[CH3:1])=[O:8]

Participants

6

Reactant 4

HCID 1049PyridineHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 516892Sodium BicarbonateHCID 27952174-Methyloxazole-5-carbonyl chloride

Product 1

HCID 18925369N-Methoxy-N,4-dimethyloxazole-5-carboxamide

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

4-Methyl-5-oxazolecarbonyl chloride (15 g) and N,O-dimethylhydroxylamine hydrochloride (11 g) in dry chloroform (100 ml) were cooled to 0° C. and dry pyridine (28.5 g) was added. The mixture was allowed to warm to room temperature. After 30 minutes aqueous sodium hydrogen carbonate was added and the organic layer separated. The aqueous layer was extracted with dichloromethane. The combined organic layers were washed, dried and evaporated. The residue was purified by flash chromatography to yield the title compound as a white solid. M.p. 59°-60° C.

Workup

  1. customthe organic layer separated
  2. extractionThe aqueous layer was extracted with dichloromethane
  3. washThe combined organic layers were washed
  4. customdried
  5. customevaporated
  6. customThe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-5e7672e863b54b3087d06ae6fbf739fb
Source dataset
uspto-grants-1997_03
Patent number
US05607956

Linked notes

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