Ammonia → (Dimethyl-1,2-oxazol-4-yl)methanamine

Reaction equation

Cl[CH2:2][C:3]1[C:4]([CH3:9])=[N:5][O:6][C:7]=1[CH3:8].[NH3:10]>>[NH2:10][CH2:2][C:3]1[C:4]([CH3:9])=[N:5][O:6][C:7]=1[CH3:8]

Participants

Reactant 2

HCID 222Ammonia

HCID 88246Isoxazole, 4-(chloromethyl)-3,5-dimethyl-

Product 1

HCID 11018874(Dimethyl-1,2-oxazol-4-yl)methanamine

Procedure

4-Chloromethyl-3,5-dimethylisoxazole (700 mg, 4.8 mmol) is suspended in concentrated aqueous ammonia at 20-25 degrees C., and vigorously stirred overnight. The reaction mixture is extracted with isopropyl alcohol/chloroform (10/90, 2×). The combined organic phases are concentrated under nitrogen flow. The residue is purified by flash chromatography methanol/methylene chloride (5-20%, 1% triethylamine) to give the title compound, MR (CDCl3, 300 MHz) delta 3.62, 2.37, 2.29, and 1.44.

Workup

customvigorously stirred overnight
extractionThe reaction mixture is extracted with isopropyl alcohol/chloroform (10/90, 2×)
concentrationThe combined organic phases are concentrated under nitrogen flow
customThe residue is purified by flash chromatography methanol/methylene chloride (5-20%, 1% triethylamine)

Sources & evidence

ORD record: ord-baadfe228970474f9ccf855c160cc0da
Source dataset: uspto-grants-2009_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07498436B2

Reaction notes

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