Azobisisobutyronitrile → HCID 131718089, compound

HRID 2255533Notes

Reaction equation

HRID 2255533 reaction equation
[C:1]1([C:7]([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[N:8]2[C:12]([C:13]3[C:18]([C:19]4[CH:24]=[CH:23][C:22]([CH3:25])=[CH:21][CH:20]=4)=[CH:17][CH:16]=[C:15]([F:26])[CH:14]=3)=[N:11][N:10]=[N:9]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Br:39]N1C(=O)CCC1=O.CC(N=NC(C#N)(C)C)(C#N)C>C(Cl)(Cl)(Cl)Cl>[C:33]1([C:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)([C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=2)[N:8]2[C:12]([C:13]3[C:18]([C:19]4[CH:24]=[CH:23][C:22]([CH2:25][Br:39])=[CH:21][CH:20]=4)=[CH:17][CH:16]=[C:15]([F:26])[CH:14]=3)=[N:11][N:10]=[N:9]2)[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1

Participants

5

Reactant 3

HCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 131718090HCID 131718090, compound

Product 1

HCID 131718089HCID 131718089, compound

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

To a solution of N-Triphenylmethyl-5-(4-fluoro-4'-methyl-biphen-2-yl)tetrazole (454.4 mg; 0.9161 mmol) in dry CCl4 (8 mL) was added N-bromosuccinimide (179.2 mg; 1.1 eq) and a catalytic amount of AIBN. The reaction was heated to reflux (105°-115°) under N2. After 3 hrs. the reaction was cooled and filtered through a cotton plugged pipet to remove the succinimide formed. The solvent was removed and replaced by EtOAc/Et2O. The reaction was washed with 1N NaOH and brine. The organic solution was dried over anhydrous MgSO4, filtered, and concentrated in vacuo to afford the product. The crude product was used in the next reaction.

Workup

  1. temperatureThe reaction was heated
  2. temperatureto reflux (105°-115°) under N2
  3. temperaturethe reaction was cooled
  4. filtrationfiltered through a cotton
  5. customto remove the succinimide
  6. customformed
  7. customThe solvent was removed
  8. washThe reaction was washed with 1N NaOH and brine
  9. dry with materialThe organic solution was dried over anhydrous MgSO4
  10. filtrationfiltered
  11. concentrationconcentrated in vacuo
  12. customto afford the product

Sources & evidence

ORD record
ord-4138e63ce9414e8cb4788aea39893571
Source dataset
uspto-grants-1993_08
Patent number
US05240928

Reaction notes

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