Methylhydrazine → HCID 90025102, compound

Temperature

100 °C

A mixture of (Z)-methyl N,N-dimethyl-N′-(3-methylbut-2-enoyl)carbamimidothioate (2.41 g, 12.0 mmol, Eq: 1.00) and methylhydrazine (5.54 g, 6.34 ml, 120 mmol, Eq: 10) was heated to 100° C. for 30 minutes. The mixture was dissolved in ethyl acetate and washed with water 3 times and once with brine. The organic layer was separated, dried over magnesium sulfate, filtrated and evaporated affording dimethyl-[1-methyl-5-(2-methyl-propenyl)-1H-[1,2,4]triazol-3-yl]-amine (824 mg/38.0%) as a yellow liquid. A mixture of N,N,1-trimethyl-5-(2-methylprop-1-enyl)-1H-1,2,4-triazol-3-amine (824 mg, 4.57 mmol, Eq: 1.00), osmium tetroxide 4% aq. (872 mg, 872 μl, 137 μmol, Eq: 0.03), sodium periodate (3.91 g, 18.3 mmol, Eq: 4) and benzyltriethylammonium chloride (416 mg, 1.83 mmol, Eq: 0.4) in dioxane (42 ml) and water (13 ml) was stirred for 2 hours at 60° C. The mixture was diluted with ethyl acetate and washed with 2× water and brine. The organic layer was separated, dried over magnesium sulfate, filtrated and evaporated affording 1.0 g dark brown oil. The crude material was applied on silicagel and purified by flash chromatography over a 50 g silicagel column using ethyl acetate/methanol 0-10% as eluent affording 5-dimethylamino-2-methyl-2H-[1,2,4]triazole-3-carbaldehyde (127 mg/60.0%) as a brown oil. MS: m/e=155.3 (M+H+)

1. washwashed with water 3 times and once with brine
2. customThe organic layer was separated
3. dry with materialdried over magnesium sulfate
4. filtrationfiltrated
5. customevaporated

ORD record

ord-4b5ea3dd5dcb46dd83b94d87dd908f1b

Source dataset

uspto-grants-2016_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09394311B2