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

HRID 1968377Notes

Reaction equation

HRID 1968377 reaction equation
[Br:1][C:2]1[CH:23]=[CH:22][C:5]([C:6]([NH:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[NH:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=O)=[CH:4][CH:3]=1.P(Cl)(Cl)(Cl)=O>O1CCOCC1>[Br:1][C:2]1[CH:23]=[CH:22][C:5]([C:6]2[N:15]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[C:10]3[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=3[N:8]=2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 230940554-Bromo-N-(2-(phenylamino)phenyl)benzamide

Product 1

HCID 230940702-(4-Bromophenyl)-1-phenyl-1H-benzo(d)imidazoleYield 90.3%

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 phosphorus oxychloride (POCl3) (9.2 mL, 100 mmol) slowly. The whole was then heated at 100° C. overnight. After cooling to RT, the mixture was poured into ice (200 g) with stirring. Filtration, followed by recrystallization in DCM/hexanes gave a pale grey solid 2 (8.2 g, in 90% yield).

Workup

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

Sources & evidence

ORD record
ord-ee43d749873f48fda7e03a40f3de9103
Source dataset
uspto-grants-2013_04
Patent number
US08426040B2

Reaction notes

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