Nitrogen → 2-(2-((4-Amino-2H-1,2,3-triazol-2-yl)methyl)oxazol-4-yl)propan-2-ol

HRID 527248Notes

Reaction equation

N#N.[N+:3]([C:6]1[CH:10]=[N:9][N:8]([CH2:11][C:12]2[O:13][CH:14]=[C:15]([C:17]([OH:20])([CH3:19])[CH3:18])[N:16]=2)[N:7]=1)([O-])=O.[NH4+].[Cl-]>CCO.O.[Fe]>[NH2:3][C:6]1[CH:10]=[N:9][N:8]([CH2:11][C:12]2[O:13][CH:14]=[C:15]([C:17]([OH:20])([CH3:18])[CH3:19])[N:16]=2)[N:7]=1

Participants

Conditions

Temperature: 85 °C

Procedure

In a flame dried round-bottomed flask equipped with a magnetic stir bar and under inert atmosphere (N2), a mixture of 2-(2-((4-nitro-2H-1,2,3-triazol-2-yl)methyl)oxazol-4-yl)propan-2-ol (2.40 g, 10.75 mmol), iron powder (1.82 g, 32.25 mmol) and NH4Cl (2.90 g, 53.76 mmol) in a mixture of EtOH (70 mL) and water (35 mL) was stirred at 85° C. for 15 min. The reaction mixture was filtered while hot and concentrated under reduced pressure. CH2Cl2 (110 mL) was added followed by 1N NaOH (65 mL). The layers were separated and the aq. layer was extracted with CH2Cl2 (5×50 mL). The combined org. extracts were dried over MgSO4, filtered, and the solvents were removed under reduced pressure to give the title compound as an orange oil. LC-MS-conditions 06: tR=0.35 min; [M+H]+=224.00.

Workup

filtrationThe reaction mixture was filtered while hot and
concentrationconcentrated under reduced pressure
additionCH2Cl2 (110 mL) was added
customThe layers were separated
extractionthe aq. layer was extracted with CH2Cl2 (5×50 mL)
dry with materialextracts were dried over MgSO4
filtrationfiltered
customthe solvents were removed under reduced pressure

Sources & evidence

ORD record: ord-249fc07b6a694ffc9423c8ed9637ac9a
Source dataset: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09346793B2

Reaction notes

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