Nitrogen → 2-((2-(methoxymethyl)thiazol-5-yl)methyl)-2H-1,2,3-triazol-4-amine

Temperature

85 °C

In a flame dried round-bottomed flask equipped with a magnetic stir bar and under inert atmosphere (N2), a mixture of 2-(methoxymethyl)-5-((4-nitro-2H-1,2,3-triazol-2-yl)methyl)thiazole (109 mg, 0.43 mmol), iron powder (72 mg, 1.28 mmol) and NH4Cl (115 mg, 2.14 mmol) in a mixture of EtOH (2.0 mL) and water (1.0 mL) was stirred at 85° C. for 15 min. The reaction mixture was filtered while hot and concentrated under reduced pressure. CH2Cl2 (5 mL) was added followed by 1N NaOH (5 mL). The layers were separated and the aq. layer was extracted with CH2Cl2 (2×5 mL). The combined org. extracts were dried over Na2SO4, filtered, and the solvents were removed under reduced pressure to give the title compound as a yellow oil. LC-MS-conditions 07: tR=0.50 min; [M+H]+=225.93.

1. filtrationThe reaction mixture was filtered while hot and
2. concentrationconcentrated under reduced pressure
3. additionCH2Cl2 (5 mL) was added
4. customThe layers were separated
5. extractionthe aq. layer was extracted with CH2Cl2 (2×5 mL)
6. dry with materialextracts were dried over Na2SO4
7. filtrationfiltered
8. customthe solvents were removed under reduced pressure

ORD record

ord-63b8dd8d0f814c148c2c9bc68e85b371

Source dataset

uspto-grants-2014_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08846733B2