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

HRID 82814Notes

Reaction equation

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

Participants

Conditions

Temperature: 100 °C

Procedure

In a flame dried round-bottomed flask equipped with a magnetic stir bar and under inert atmosphere (N2), a mixture of 2-(methoxymethyl)-4-((4-nitro-2H-1,2,3-triazol-2-yl)methyl)thiazole (200 mg, 0.78 mmol), iron powder (133 mg, 2.35 mmol) and NH4Cl (212 mg, 3.92 mmol) in a mixture of EtOH (10.0 mL) and water (5.0 mL) was stirred at 100° C. for 2 h. The reaction mixture was filtered while hot and concentrated under reduced pressure. CH2Cl2 (40 mL) was added followed by 1N NaOH (20 mL). The layers were separated and the aq. layer was extracted with CH2Cl2 (2×10 mL). The combined org. extracts were dried over MgSO4, filtered, and the solvents were removed under reduced pressure to give the title compound which was purified by preparative HPLC to give a colorless 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 (40 mL) was added
customThe layers were separated
extractionthe aq. layer was extracted with CH2Cl2 (2×10 mL)
dry with materialextracts were dried over MgSO4
filtrationfiltered
customthe solvents were removed under reduced pressure

Sources & evidence

ORD record: ord-835b6d442a6240e8bce5e9a45080a93a
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08846733B2

Reaction notes

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