Benzoyl Peroxide → 7-(1-Bromoethyl)-1,2,4-triazolo[1,5-a]pyrimidine

HRID 1290802Notes

Reaction equation

HRID 1290802 reaction equation
[CH2:1]([C:3]1[N:8]2[N:9]=[CH:10][N:11]=[C:7]2[N:6]=[CH:5][CH:4]=1)[CH3:2].[Br:12]N1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>ClC(Cl)(Cl)Cl>[Br:12][CH:1]([C:3]1[N:8]2[N:9]=[CH:10][N:11]=[C:7]2[N:6]=[CH:5][CH:4]=1)[CH3:2]

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 189193537-Ethyl-1,2,4-triazolo[1,5-a]pyrimidine

Product 1

HCID 189193517-(1-Bromoethyl)-1,2,4-triazolo[1,5-a]pyrimidine

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

A mixture of 7-ethyl-1,2,4-triazolo[1,5-a]pyrimidine (10.5 g), N-bromosuccinimide (12.63 g), dibenzoylperoxide (0.3 g) and tetrachloromethane (270 ml) was heated under reflux for 5 hours with stirring. The mixture was filtered and a crude product was obtained by evaporation of the solvent from the filtrate. This was purified by recrystallisation from tetrachloromethane to give 7-(1-bromoethyl)-1,2,4-triazolo[1,5-a]pyrimidine. Yield 10.8 g.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 5 hours
  3. filtrationThe mixture was filtered
  4. customa crude product was obtained by evaporation of the solvent from the filtrate
  5. customThis was purified by recrystallisation from tetrachloromethane

Sources & evidence

ORD record
ord-500a3da8126445c6a19de442eeceb3b4
Source dataset
uspto-grants-1998_05
Patent number
US05753665

Reaction notes

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