Water → 7-bromo-2-chloro-1-methyl-1H-1,3-benzodiazole

HRID 1698541Notes

Reaction equation

HRID 1698541 reaction equation
[Br:1][C:2]1[C:7]2[N:8]([CH3:12])[C:9](=O)[NH:10][C:6]=2[CH:5]=[CH:4][CH:3]=1.O.P(Cl)(Cl)([Cl:16])=O>>[Br:1][C:2]1[C:7]2[N:8]([CH3:12])[C:9]([Cl:16])=[N:10][C:6]=2[CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 962WaterHCID 24813Phosphorus oxychlorideHCID 596354707-bromo-1-methyl-1,3-dihydro-2H-benzimidazol-2-one

Product 1

HCID 672731127-bromo-2-chloro-1-methyl-1H-1,3-benzodiazole

Conditions

Temperature
110 °C

Procedure

7-Bromo-1-methyl-1,3-dihydro-2H-benzimidazol-2-one (2.20 g, 9.69 mmol) was dissolved in 30 mL of phosphorous oxychloride and the mixture was heated at 110° C. for 2 days. The reaction allowed to cool to room temperature, poured into water with an ice, and stirred for 1 h. The aqueous solution was extracted with ethyl acetate. The extract was washed with aqueous sodium bicarbonate, dried over magnesium sulfate, filtered and concentrated in vacuo to give 2.32 g of the title compound, which was used in the next reaction without further purification.

Workup

  1. temperatureto cool to room temperature
  2. extractionThe aqueous solution was extracted with ethyl acetate
  3. washThe extract was washed with aqueous sodium bicarbonate
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-a8c4e69360bb4f4cabe0876abfe53090
Source dataset
uspto-grants-2012_04
Patent number
US08163935B2

Reaction notes

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