Benzoyl Peroxide → HCID 12401525, compound

HRID 1763938Notes

Reaction equation

HRID 1763938 reaction equation
[C:1]1([CH3:16])[CH:6]=[CH:5][C:4]([C:7]2[N:15]=[C:10]3[CH:11]=[CH:12][CH:13]=[CH:14][N:9]3[N:8]=2)=[CH:3][CH:2]=1.[Br:17]N1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl>[Br:17][CH2:16][C:1]1[CH:2]=[CH:3][C:4]([C:7]2[N:15]=[C:10]3[CH:11]=[CH:12][CH:13]=[CH:14][N:9]3[N:8]=2)=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 12308360[1,2,4]Triazolo[1,5-a]pyridine, 2-(4-methylphenyl)-

Product 1

HCID 12401525HCID 12401525, compound

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Conditions

Temperature
20 °C

Procedure

41.85 g of 2-(p-tolyl)-s-triazolo[1,5-a]pyridine (26) are dissolved at 50° C. in 1,200 ml of dry carbon tetrachloride. 37.4 g of N-bromosuccinimide and 1 g of dibenzoyl peroxide are then added and the mixture is warmed gradually to the boil while stirring well and with exposure to a 400 W lamp. The reaction mixture is kept under reflux for 4 hours and is then cooled to 20° C. and the product which has precipitated is filtered off with suction. The succinimide is removed by washing with a large amount of water and the material on the suction filter is dried. This gives 39.2 g (58% of theory) of compound (I) in the form of a pale beige powder with a melting point of 192° to 193° C. After recrystallising twice from toluene, 32.3 g (56.1% of theory) of small, virtually colourless, glossy needles with a melting point of 195.5° to 196° C. are obtained.

Workup

  1. temperaturethe mixture is warmed gradually to the boil
  2. temperatureunder reflux for 4 hours
  3. customthe product which has precipitated
  4. filtrationis filtered off with suction
  5. customThe succinimide is removed
  6. washby washing with a large amount of water
  7. filtrationthe material on the suction filter
  8. customis dried
  9. customAfter recrystallising twice from toluene, 32.3 g (56.1% of theory) of small, virtually colourless, glossy needles with a melting point of 195.5° to 196° C.
  10. customare obtained

Sources & evidence

ORD record
ord-9d836d5c00654700be96133baaf83927
Source dataset
uspto-grants-1978_09
Patent number
US04113937

Reaction notes

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