p-Toluenesulfonic acid monohydrate → 6-bromo-1-phenyl-1H-benzo[d]imidazole

HRID 1051463Notes

Reaction equation

HRID 1051463 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([NH:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[C:5]([NH2:15])=[CH:4][CH:3]=1.[CH3:16]C1C=CC(S(O)(=O)=O)=CC=1.O>C(OC)(OC)OC>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[N:15]=[CH:16][N:8]([C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=3)[C:6]=2[CH:7]=1

Participants

4

Reactant 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 129301705-bromo-N1-phenylbenzene-1,2-diamine

Product 1

HCID 202668606-bromo-1-phenyl-1H-benzo[d]imidazole

Reagents, catalysts & solvents 1

HCID 9005Trimethyl orthoformateSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 5-bromo-N1-phenylbenzene-1,2-diamine (650 mg, 2.47 mmol) in HC(OMe)3 (15 mL) was added TsOH.H2O (38 mg, 0.2 mmol). The mixture was stirred at 100° C. for 4 h. Upon completion, the reaction solution was concentrated, the residue was extracted with EtOAc and washed with water. The organic layer was concentrated to give the crude 6-bromo-1-phenyl-1H-benzo[d]imidazole which was used in next step without further purification. LCMS (m/z): 273.1/274.1 [M+H]+/[M+2H]+

Workup

  1. concentrationUpon completion, the reaction solution was concentrated
  2. extractionthe residue was extracted with EtOAc
  3. washwashed with water
  4. concentrationThe organic layer was concentrated

Sources & evidence

ORD record
ord-6c92c3c223e14c40ba4433ce10fb6d21
Source dataset
uspto-grants-2016_07
Patent number
US09388173B2

Reaction notes

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