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

HRID 82810Notes

Reaction equation

N#N.[CH3:3][O:4][CH2:5][C:6]1[N:7]=[C:8]([CH2:11][N:12]2[N:16]=[C:15]([N+:17]([O-])=O)[CH:14]=[N:13]2)[S:9][CH:10]=1.[NH4+].[Cl-]>CCO.O.[Fe]>[CH3:3][O:4][CH2:5][C:6]1[N:7]=[C:8]([CH2:11][N:12]2[N:16]=[C:15]([NH2:17])[CH:14]=[N:13]2)[S:9][CH:10]=1

Participants

Conditions

Temperature: 75 °C

Procedure

In a flame dried round-bottomed flask equipped with a magnetic stir bar and under inert atmosphere (N2), a mixture of 4-(methoxymethyl)-2-((4-nitro-2H-1,2,3-triazol-2-yl)methyl)thiazole (85 mg, 0.31 mmol), iron powder (66 mg, 1.17 mmol) and NH4Cl (108 mg, 2.0 mmol) in a mixture of EtOH (2.0 mL) and water (1.0 mL) was stirred at 75° C. for 25 min. The reaction mixture was filtered while hot and concentrated under reduced pressure. CH2Cl2 (15 mL) was added followed by 1N NaOH (10 mL). The layers were separated and the aq. layer was extracted with CH2Cl2 (3×10 mL). The combined org. extracts were dried over MgSO4, filtered, and the solvents were removed under reduced pressure to give the title compound as a yellow oil. LC-MS-conditions 07: tR=0.47 min, [M+H]+=226.30.

Workup

filtrationThe reaction mixture was filtered while hot and
concentrationconcentrated under reduced pressure
additionCH2Cl2 (15 mL) was added
customThe layers were separated
extractionthe aq. layer was extracted with CH2Cl2 (3×10 mL)
dry with materialextracts were dried over MgSO4
filtrationfiltered
customthe solvents were removed under reduced pressure

Sources & evidence

ORD record: ord-381a301b268240e5a83a571f6437d33f
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08846733B2

Reaction notes

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