N-bromobutanimide → HCID 15428566, compound

HRID 1584799Notes

Reaction equation

HRID 1584799 reaction equation
BrN1C(=[O:7])CCC1=O.[CH3:9][C:10]1[C:18]2[O:17][CH:16]=[CH:15][C:14]=2[CH:13]=[C:12]([N:19]2[CH:23]=[N:22][N:21]=[N:20]2)[CH:11]=1>C(Cl)(Cl)(Cl)Cl.[W]>[N:19]1([C:12]2[CH:11]=[C:10]([CH:9]=[O:7])[C:18]3[O:17][CH:16]=[CH:15][C:14]=3[CH:13]=2)[CH:23]=[N:22][N:21]=[N:20]1

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 21220901HCID 21220901, compound

Product 1

HCID 15428566HCID 15428566, compound

Reagents, catalysts & solvents 2

HCID 23964TungstenCatalystHCID 5943Carbon TetrachlorideSolvent

Procedure

N-Bromosuccinimide (180 mg) was added to a hot solution of 1-(7-methyl-benzofuran-5-yl)-1H-tetrazole and azoisobutyronitrile (35 mg) in carbon tetrachloride (10 ml) and the mixture heated at reflux whilst irradiating with a 60 W tungsten lamp for 4 hours. The mixture was evaporated in vacuo, the solid residue dissolved in acetonitrile (5 ml) then added dropwise to a solution of N-methyl morpholine-N-oxide (0.2 g) in acetonitrile (10 ml) containing 4 Å sieves. The reaction mixture was stirred for 16 h at room temperature, filtered, the solvent removed in vacuo and the residue purified by FCC eluting with ether-hexane (2:1) to give the title compound as a white solid (56 mg) m.p. 174-175°.

Workup

  1. temperaturethe mixture heated
  2. temperatureat reflux
  3. customThe mixture was evaporated in vacuo
  4. dissolutionthe solid residue dissolved in acetonitrile (5 ml)
  5. additionthen added dropwise to a solution of N-methyl morpholine-N-oxide (0.2 g) in acetonitrile (10 ml)
  6. additioncontaining 4 Å sieves
  7. filtrationfiltered
  8. customthe solvent removed in vacuo
  9. customthe residue purified by FCC
  10. washeluting with ether-hexane (2:1)

Sources & evidence

ORD record
ord-db9d393ff04e4480a1b6189d88203cb5
Source dataset
uspto-grants-1999_08
Patent number
US05935972

Reaction notes

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