Phosphorus oxychloride → 2-(4-Bromophenyl)-1-phenyl-1H-benzo(d)imidazole

HRID 1912161Notes

Reaction equation

HRID 1912161 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2O[C:10]3[CH:16]=[CH:15][CH:14]=[CH:13][C:11]=3[N:12]=2)=[CH:4][CH:3]=1.P(Cl)(Cl)(Cl)=O>O1CCOCC1>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]([C:11]3[CH:13]=[CH:14][CH:15]=[CH:16][CH:10]=3)[C:10]3[CH:16]=[CH:15][CH:14]=[CH:13][C:11]=3[N:12]=2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 128467152-(4-Bromophenyl)benzo(d)oxazole

Product 1

HCID 230940702-(4-Bromophenyl)-1-phenyl-1H-benzo(d)imidazoleYield 90%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

To a suspension of amide 1 (9.6 g, 26 mmol) in anhydrous 1,4-dioxane (100 mL) was added phosphorous oxychloride (POCl3) (9.2 mL, 100 mmol) slowly. The whole was then heated at 100° C. overnight. After cooling to r.t., the mixture was poured into ice (200 g) with stirring. Filtration, followed by recrystallization in DCM/hexanes gave a pale grey solid (Compound 5) (8.2 g, in 90% yield).

Workup

  1. temperatureAfter cooling to r.t.
  2. filtrationFiltration
  3. customfollowed by recrystallization in DCM/hexanes

Sources & evidence

ORD record
ord-15307e497f8a4aadb0d3846bddcc0cf6
Source dataset
uspto-grants-2013_12
Patent number
US08604689B2

Reaction notes

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