N-bromobutanimide → 5-[4-(Bromomethyl)phenyl]-2-ethyl-1,2,3,4-tetraazole

HRID 2245319Notes

Reaction equation

HRID 2245319 reaction equation
[CH2:1]([N:3]1[N:7]=[N:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([CH3:14])=[CH:10][CH:9]=2)=[N:4]1)[CH3:2].[Br:15]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>[Br:15][CH2:14][C:11]1[CH:12]=[CH:13][C:8]([C:5]2[N:6]=[N:7][N:3]([CH2:1][CH3:2])[N:4]=2)=[CH:9][CH:10]=1

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 207099322-Ethyl-5-(4-methylphenyl)-1,2,3,4-tetraazole

Product 1

HCID 686826535-[4-(Bromomethyl)phenyl]-2-ethyl-1,2,3,4-tetraazoleYield 103.7%

Reagents, catalysts & solvents 2

HCID 7187Benzoyl PeroxideCatalystHCID 5943Carbon TetrachlorideSolvent

Procedure

A solution of 18.8 grams (0.100 mole) of 2-ethyl-5-(4-methylphenyl)-1,2,3,4-tetraazole in 156 mL of carbon tetrachloride was stirred, and 19.6 grams (0.110 mole) of N-bromosuccinimide, followed by 0.24 gram (0.001 mole) of benzoyl peroxide were added. Upon completion of addition, the reaction mixture was heated to reflux where it stirred for 90 minutes. After this time the reaction mixture was cooled and filtered. The filtrate was concentrated under reduced pressure, yielding 27.7 grams of the subject compound. The NMR spectrum was consistent with the proposed structure.

Workup

  1. additionwere added
  2. additionUpon completion of addition
  3. temperaturethe reaction mixture was heated
  4. temperatureto reflux where it
  5. temperatureAfter this time the reaction mixture was cooled
  6. filtrationfiltered
  7. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-feee1914c47f4592b66786ab9aa330c2
Source dataset
uspto-grants-2010_03
Patent number
US07683070B2

Reaction notes

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