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Acetic Acid → 4-bromo-3-(2H-1,2,3-triazol-2-yl)thiophene-2-amine

HRID 2098080
Notes
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Reaction equation

HRID 2098080 reaction equation
[Br:1][C:2]1[C:3]([N:10]2[N:14]=[CH:13][CH:12]=[N:11]2)=[C:4]([N+:7]([O-])=O)[S:5][CH:6]=1.C(O)(=O)C>[Fe].O>[Br:1][C:2]1[C:3]([N:10]2[N:14]=[CH:13][CH:12]=[N:11]2)=[C:4]([NH2:7])[S:5][CH:6]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 687845502-(4-bromo-2-nitrothiophen-3-yl)-2H-1,2,3-triazole

Product 1

HCID 687570274-bromo-3-(2H-1,2,3-triazol-2-yl)thiophene-2-amineYield 66.4%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 962WaterSolvent

Procedure

A mixture of 2-(4-bromo-2-nitrothiophen-3-yl)-2H-1,2,3-triazole (0.59 g, 2.15 mmol), iron powder (0.75 g, 13.38 mmol), glacial acetic acid (8.4 mL) and H2O (1.2 mL) was heated in an oil bath set at 70° C. under condenser with N2 (g) inlet for 1 h. Purification by flash chromatography (silica, 40:60 ethyl acetate/hexane) gave 4-bromo-3-(2H-1,2,3-triazol-2-yl)thiophene-2-amine (0.35 g, 66%). Retention time (min)=1.540, method [4], MS (ESI) 246.9 (M+H).

Workup

  1. temperaturewas heated in an oil bath
  2. customPurification by flash chromatography (silica, 40:60 ethyl acetate/hexane)

Sources & evidence

ORD record
ord-e7f08422abb849b7aac32cac679e5641
Source dataset
uspto-grants-2013_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08450363B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes