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

HRID 1289049Notes

Reaction equation

HRID 1289049 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 (15g) and N,O-dimethylhydroxylamine hydrochloride (11 g) in dry chloroform (looml) were cooled to OOC and dry pyridine (28.5g) 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. 1H Nmr (CDC3) 2.5, 3.34 and 3.82 (each 3H, s) and 7.86 (1H, S) ppm. Found: C, 49.0; H, 5.6; N, 16.4. C7H10N2O3 requires C, 49.4; H, 5.9; N, 16.5%

Workup

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

Sources & evidence

ORD record
ord-b7caea644fae4f67826b024604848b90
Source dataset
uspto-grants-1998_05
Patent number
US05747515

Reaction notes

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