Acetic Acid → 5-(4-Bromophenyl)-1H-1,2,4-triazole

HRID 538988Notes

Reaction equation

HRID 538988 reaction equation
O.[NH2:2]N.C(O)(=O)C.[Br:8][C:9]1[CH:21]=[CH:20][C:12]([C:13](/[N:15]=[CH:16]/[N:17](C)C)=O)=[CH:11][CH:10]=1>>[Br:8][C:9]1[CH:21]=[CH:20][C:12]([C:13]2[NH:2][N:17]=[CH:16][N:15]=2)=[CH:11][CH:10]=1

Participants

4

Reactant 3

HCID 176Acetic AcidHCID 24654Hydrazine hydrate (1:1)HCID 178484323HCID 178484323, compound

Product 1

HCID 469487345-(4-Bromophenyl)-1H-1,2,4-triazoleYield 66.5%

Conditions

Temperature
90 °C

Procedure

To a solution of hydrazine hydrate (1.96 mL, 40.4 mmol) in acetic acid (91.9 mL, 36.8 mmol) was added (E)-4-bromo-N-((dimethylamino)methylene)benzamide (9.38 g, 36.8 mmol) and the mixture stirred at 90° C. for 1.5 hours. The reaction mixture was concentrated to about 10 mL and diluted with ether (50 mL). The resulting white solid was collected by vacuum filtration, rinsing with excess ether, and dried to afford 5-(4-bromophenyl)-1H-1,2,4-triazole (5.48 g, 66%) which was carried on without further purification. LCMS (APCI+) m/z 224, 226 [M+H]+.

Workup

  1. concentrationThe reaction mixture was concentrated to about 10 mL
  2. additiondiluted with ether (50 mL)
  3. filtrationThe resulting white solid was collected by vacuum filtration
  4. washrinsing with excess ether
  5. customdried

Sources & evidence

ORD record
ord-a03b0807d0e747069a523bbc344bccc7
Source dataset
uspto-grants-2014_10
Patent number
US08865726B2

Reaction notes

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