N-bromobutanimide → HCID 13021433, compound

HRID 262240Notes

Reaction equation

HRID 262240 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][N:5]2[N:8]=[N:9][N:10]=[C:4]2[CH:3]=1.[Br:11]N1C(=O)CCC1=O>C1C=CC=CC=1.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>[Br:11][CH2:1][C:2]1[CH:7]=[CH:6][N:5]2[N:8]=[N:9][N:10]=[C:4]2[CH:3]=1

Participants

5

Reactant 2

HCID 67184N-bromobutanimide2×HCID 2430217-Methyltetrazolo[1,5-a]pyridine

Product 1

HCID 13021433HCID 13021433, compound

Reagents, catalysts & solvents 2

HCID 7187Benzoyl PeroxideCatalystHCID 241BenzeneSolvent

Procedure

7-Methyl tetrazolo [1,5-a]pyridine [Boyer, et al., J. Am. Chem. Soc., 82, 2218 (1960](23 g, 173 mmole), N-bromosuccinimide (30.6 g, 173 mmole) and benzoyl peroxide (100 mg) in 1.5 liters of benzene is refluxed overnight. More N-bromosuccinimide (15.3 g, 86.5 mole) is added and the reflux is maintained for several hours. The mixture is cooled and washed with 100 ml 20% sodium hydroxide and then with water. It is dried over calcium chloride, evaporated to dryness to yield 36.4 g of a mixture of 7-bromomethyltetrazolo [1,5-a]pyridine (63%) 7-dibromomethyltetrazolo [1,5-a]pyridine (24%) and 7-methyltetrazolo [1,5-a]pyridine (13%). Two triturations of this mixture with 500 ml of ether-hexane 1:1 (v/v) affords 25 g of a mixture consisting of 82% monobromo derivative, 13% dibromo derivative and 5% of starting material. This mixture is used for the next step.

Workup

  1. temperaturethe reflux is maintained for several hours
  2. temperatureThe mixture is cooled
  3. washwashed with 100 ml 20% sodium hydroxide
  4. dry with materialIt is dried over calcium chloride
  5. customevaporated to dryness

Sources & evidence

ORD record
ord-197f4278153d4c45a08b05608695f4ed
Source dataset
uspto-grants-1979_05
Patent number
US04153715

Reaction notes

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