Water → HCID 11724483, compound

HRID 1742665Notes

Reaction equation

HRID 1742665 reaction equation
[Br:1][C:2]1[CH:18]=[CH:17][C:5]2[S:6][CH2:7][C:8]3[CH:16]=[CH:15][CH:14]=[CH:13][C:9]=3C(C#N)[C:4]=2[CH:3]=1.O.Cl.[C:21]([OH:24])(=[O:23])[CH3:22]>>[Br:1][C:2]1[CH:18]=[CH:17][C:5]2[S:6][CH2:7][C:8]3[CH:16]=[CH:15][CH:14]=[CH:13][C:9]=3[CH:22]([C:21]([OH:24])=[O:23])[C:4]=2[CH:3]=1

Participants

4

Reactant 3

HCID 962WaterHCID 10358361HCID 10358361, compoundHCID 22641269Acetate-hydrochloric acid

Product 1

HCID 11724483HCID 11724483, compound

Procedure

After 4.72 g of 2-bromo-11-cyano-6,11-dihydrodibenzo[b,e]thiepine was dissolved in 90 ml of hydrochloric acid-acetic acid (1:2), the mixture was heated under reflux for 48 hours. The reaction mixture was allowed to stand at room temperature, and 50 ml of water was added to the reaction mixture, and extracted with ethyl acetate. The extract was washed with water. The organic layer was extracted 3 times with saturated sodium bicarbonate aqueous solution. The aqueous layer was adjusted to pH 2 with 4N hydrochloric acid, and extracted with ethyl acetate. The extract was washed with water and saturated sodium chloride aqueous solution successively, dried over anhydrous magnesium sulfate and concentrated to dryness under reduced pressure to obtain 2.68 g of 2-bromo-6,11-dihydrodibenzo[b,e]thiepin-11-carboxylic acid.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 48 hours
  3. customto stand at room temperature
  4. extractionextracted with ethyl acetate
  5. washThe extract was washed with water
  6. extractionThe organic layer was extracted 3 times with saturated sodium bicarbonate aqueous solution
  7. extractionextracted with ethyl acetate
  8. washThe extract was washed with water and saturated sodium chloride aqueous solution successively
  9. dry with materialdried over anhydrous magnesium sulfate
  10. concentrationconcentrated to dryness under reduced pressure

Sources & evidence

ORD record
ord-afad0f73ea2e4f0bbc6c0c24357c05af
Source dataset
uspto-grants-1994_08
Patent number
US05340807

Reaction notes

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