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Nitrogen → 1-(2-((4-amino-2H-1,2,3-triazol-2-yl)methyl)oxazol-4-yl)ethanone

HRID 42856
Notes
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Reaction equation

HRID 42856 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](=[O: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](=[O:19])[CH3:18])[N:16]=2)[N:7]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 3

HCID 947NitrogenHCID 25517Ammonium ChlorideHCID 671277401-[2-(4-Nitro-[1,2,3]triazol-2-ylmethyl)-oxazol-4-yl]-ethanone

Product 1

HCID 673655881-(2-((4-amino-2H-1,2,3-triazol-2-yl)methyl)oxazol-4-yl)ethanone

Reagents, catalysts & solvents 3

HCID 23925IronCatalyst
HCID 702
Ethanol
Solvent
HCID 962WaterSolvent

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 1-[2-(4-nitro-[1,2,3]triazol-2-ylmethyl)-oxazol-4-yl]-ethanone (48 mg, 0.20 mmol), iron powder (34 mg, 0.61 mmol) and NH4Cl (54 mg, 1.01 mmol) in a mixture of EtOH (2.0 mL) and water (1.0 mL) was stirred at 75° C. for 60 min. The reaction mixture was filtered while hot and concentrated under reduced pressure. The filtrated was dried over Na2SO4, filtered, and the solvents were removed under reduced pressure to give the title compound as a brown oil. TLC: rf (EA)=0.40. LC-MS-conditions 02: tR=0.54 min; [M+H]+=208.44.

Workup

  1. filtrationThe reaction mixture was filtered while hot and
  2. concentrationconcentrated under reduced pressure
  3. dry with materialThe filtrated was dried over Na2SO4
  4. filtrationfiltered
  5. customthe solvents were removed under reduced pressure

Sources & evidence

ORD record
ord-d8ea875d795b41dcbf0ec16ad16bf5c6
Source dataset
uspto-grants-2013_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08536209B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes