p-Toluenesulfonic acid monohydrate → 6-bromo-1-(4-methoxybenzyl)-1H-benzo[d]imidazole

HRID 1051453Notes

Reaction equation

HRID 1051453 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([NH:8][CH2:9][C:10]2[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[CH:12][CH:11]=2)[C:5]([NH2:18])=[CH:4][CH:3]=1.[CH3:19]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:18]=[CH:19][N:8]([CH2:9][C:10]3[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[CH:12][CH:11]=3)[C:6]=2[CH:7]=1

Participants

4

Reactant 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 653433435-bromo-N-(4-methoxybenzyl)benzene-1,2-diamine

Product 1

HCID 867292426-bromo-1-(4-methoxybenzyl)-1H-benzo[d]imidazoleYield 886.7%

Reagents, catalysts & solvents 1

HCID 9005Trimethyl orthoformateSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 5-bromo-N-(4-methoxybenzyl)benzene-1,2-diamine (550 mg, crude) in HC(OMe)3 (20 mL) was added TsOH.H2O (30 mg, 0.16 mmol). The mixture was stirred at 100° C. for 4 h. The reaction solution was then concentrated and the residue was washed with water and extracted with EtOAc. The organic layer was concentrated to give the desired product (450 mg, 79% yield) and the crude product used in next step without further purification. LCMS (m/z): 318.1 [M+H]+

Workup

  1. concentrationThe reaction solution was then concentrated
  2. washthe residue was washed with water
  3. extractionextracted with EtOAc
  4. concentrationThe organic layer was concentrated

Sources & evidence

ORD record
ord-a05593659c7f4edbae89920f621473e6
Source dataset
uspto-grants-2016_07
Patent number
US09388173B2

Reaction notes

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