Methylamine → N,1-dimethyl-1H-1,2,4-Triazole-3-methanamine

HRID 277330Notes

Reaction equation

Cl[CH2:2][C:3]1[N:7]=[CH:6][N:5]([CH3:8])[N:4]=1.[CH3:9][NH2:10]>O1CCOCC1>[CH3:9][NH:10][CH2:2][C:3]1[N:7]=[CH:6][N:5]([CH3:8])[N:4]=1

Participants

Conditions

Temperature: 80 °C

Procedure

A solution of 3-chloromethyl-1-methyl-1H-1,2,4-triazole (from Example 1, Step c; 600 mg, 4.6 mmol) in 40% aqueous methylamine and 1,4-dioxane (5 ml) was stirred and heated at 80° C. in a sealed tube for 16 hours. Upon cooling the whole mixture was evaporated (azeotroping with ethanol). The residue was purified by chromatography on silica gel, eluting with dichloromethane-methanol-aqueous ammonia (60:8:1→40:8:1) to give the title compound (440 mg, 80%) as a pale yellow oil. 1H NMR (250 MHz, d6-DMSO) δ 3.61 (2H, s), 3.81 (3H, s), 8.35 (1H, s); MS (ES+) m/e 127 [MH]+.

Workup

temperatureUpon cooling the whole mixture
customwas evaporated
custom(azeotroping with ethanol)
customThe residue was purified by chromatography on silica gel
washeluting with dichloromethane-methanol-aqueous ammonia (60:8:1→40:8:1)

Sources & evidence

ORD record: ord-3a17a9b7b9dd42e88672aa2a3a8610ca
Source dataset: uspto-grants-2002_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06355798B1

Reaction notes

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