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

HRID 1399839Notes

Reaction equation

HRID 1399839 reaction equation
[CH2:1]([NH:8][C:9]1[C:10]([NH2:16])=[CH:11][CH:12]=[C:13]([Br:15])[CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:17]C1C=CC(S(O)(=O)=O)=CC=1.O>C(OC)(OC)OC>[CH2:1]([N:8]1[C:9]2[CH:14]=[C:13]([Br:15])[CH:12]=[CH:11][C:10]=2[N:16]=[CH:17]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 65343042N1-benzyl-5-bromobenzene-1,2-diamine

Product 1

HCID 867292501-benzyl-6-bromo-1H-benzo[d]imidazole

Reagents, catalysts & solvents 1

HCID 9005Trimethyl orthoformateSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of N1-benzyl-5-bromobenzene-1,2-diamine (450 mg, 1.63 mmol) in HC(OMe)3 (15 mL) was added TsOH.H2O (30 mg, 0.16 mmol). The mixture was stirred at 100° C. for 4 h. The reaction solution was concentrated, and the residue was washed with water and extracted with EtOAc. The organic layer was concentrated to give the crude 1-benzyl-6-bromo-1H-benzo[d]imidazole. The crude product was used in next step without further purification. LCMS (m/z): 287.1/288.1 [M+H]+/[M+2H]+

Workup

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

Sources & evidence

ORD record
ord-3d1269d722b148eabfafcf2ffa0b7d55
Source dataset
uspto-grants-2014_12
Patent number
US08906900B2

Reaction notes

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