N-bromobutanimide → HCID 19882807, compound

HRID 846524Notes

Reaction equation

HRID 846524 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([O:9][CH:10]([CH3:12])[CH3:11])=[CH:4][C:3]=1[N:13]1[C:17](=[O:18])[N:16]([CH2:19][CH2:20][CH3:21])[N:15]=[N:14]1.[Br:22]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>[Br:22][CH2:8][C:6]1[C:5]([O:9][CH:10]([CH3:11])[CH3:12])=[CH:4][C:3]([N:13]2[C:17](=[O:18])[N:16]([CH2:19][CH2:20][CH3:21])[N:15]=[N:14]2)=[C:2]([Cl:1])[CH:7]=1

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 19882814HCID 19882814, compound2×

Product 1

HCID 19882807HCID 19882807, compoundYield 49.5%

Reagents, catalysts & solvents 2

HCID 7187Benzoyl PeroxideCatalystHCID 5943Carbon TetrachlorideSolvent

Procedure

Under a dry nitrogen atmosphere, a stirred solution of 4.4 g (0.014 mole) of 1-(2-chloro-4-methyl-5-isopropoxyphenyl)-1,4-dihydro-4-propyl-5H-tetrazol-5-one (compound 91), 2.5 g (0.014 mole) of N-bromosuccinimide, and 0.06 g (0.00025 mole) of benzoyl peroxide in 80 mL of carbon tetrachloride was heated at reflux temperature for two days. The reaction mixture was allowed to cool to room temperature, filtered, and the filtrate washed with a saturated aqueous sodium chloride solution. The washed filtrate was dried over anhydrous magnesium sulfate, filtered, and the filtrate evaporated under reduced pressure to leave an oil. The oil was crystallized from petroleum ether to yield 2.7 g of 1-(4-bromomethyl-2-chloro-5-isopropoxyphenyl)-1,4-dihydro-4-propyl-5H-tetrazol-5-one, mp 68°-70° C.

Workup

  1. temperatureat reflux temperature for two days
  2. filtrationfiltered
  3. washthe filtrate washed with a saturated aqueous sodium chloride solution
  4. dry with materialThe washed filtrate was dried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. customthe filtrate evaporated under reduced pressure
  7. customto leave an oil
  8. customThe oil was crystallized from petroleum ether

Sources & evidence

ORD record
ord-a693570d85724d089a8b7d411040a005
Source dataset
uspto-grants-1992_08
Patent number
US05136868

Reaction notes

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