Methylamine → HCID 18953964, compound

HRID 2255229Notes

Reaction equation

HRID 2255229 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[C:10]([CH2:13][CH2:14][C:15]([OH:17])=O)[O:11][CH:12]=2)=[CH:4][CH:3]=1.[CH2:18]([N:20](CC)CC)C.C(Cl)(=O)OCC.CN>C1COCC1.O>[CH3:18][NH:20][C:15](=[O:17])[CH2:14][CH2:13][C:10]1[O:11][CH:12]=[C:8]([C:5]2[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=2)[N:9]=1

Participants

7

Reactant 4

HCID 6329MethylamineHCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 18953969HCID 18953969, compound

Product 1

HCID 18953964HCID 18953964, compoundYield 89%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-(4-chlorophenyl)-2-oxazolepropionic acid (0.4 g) in THF (20 ml) were added triethylamine (0.33 ml) and ethyl chlorocarbonate (0.23 ml) at -30° C., followed by stirring for 30 minutes at the same temperature. The mixture was poured into 30% methylamine aqueous solution (10 ml), and the resultant was stirred for 15 minutes at room temperature. The reaction mixture was poured into water and extracted with ethyl acetate. The ethyl acetate layer was washed with water, dried over MgSO4 and concentrated to obtain crystals of N-methyl-4-(4-chlorophenyl)-2-oxazolepropionamide (0.375 g, 89%). Recrystallization from dichloromethane-ethanol gave colorless prism crystals of mp 169°-170° C.

Workup

  1. stirringthe resultant was stirred for 15 minutes at room temperature
  2. extractionextracted with ethyl acetate
  3. washThe ethyl acetate layer was washed with water
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-61e947193bfa4ec6b97d1ba62c83e29b
Source dataset
uspto-grants-1993_08
Patent number
US05239080

Reaction notes

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