p-Toluenesulfonic acid → 6-Bromo-1-methyl-1H-benzimidazole

HRID 1507024Notes

Reaction equation

HRID 1507024 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([NH:8][CH3:9])[C:5]([NH2:10])=[CH:4][CH:3]=1.[C:11]1(C)C=CC(S(O)(=O)=O)=CC=1>C(OC)(OC)OC>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[N:10]=[CH:9][N:8]([CH3:11])[C:6]=2[CH:7]=1

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 121982705-BROMO-N1-METHYLBENZENE-1,2-DIAMINE

Product 1

HCID 235376446-Bromo-1-methyl-1H-benzimidazoleYield 93%

Reagents, catalysts & solvents 1

HCID 9005Trimethyl orthoformateSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 5-bromo-N1-methylbenzene-1,2-diamine (7.4 g, 37 mmol) in trimethyl orthoformate (100 mL) was added p-toluenesulfonic acid (0.36 g, 1.9 mmol). The reaction mixture was heated at 100° C. for 4 h, cooled, concentrated, dissolved in ethyl acetate, washed with brine, dried over sodium sulfate and concentrated. The crude product was used in next step without further purification. (7.3 g, yield 93%) MS (ESI+) e/z: 212.1.

Workup

  1. temperaturecooled
  2. concentrationconcentrated
  3. dissolutiondissolved in ethyl acetate
  4. washwashed with brine
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated
  7. customThe crude product was used in next step without further purification

Sources & evidence

ORD record
ord-99ede51be86e4ac5a36a3c9dd3c68f11
Source dataset
uspto-grants-2015_12
Patent number
US09221794B2

Reaction notes

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