Methanol → 2-Oxo-5-chloro-6-bromo-3-benzothiazolineacetic acid

HRID 1164529Notes

Reaction equation

HRID 1164529 reaction equation
[O:1]=[C:2]1[N:6]([CH2:7][C:8]([O:10]C)=[O:9])[C:5]2[CH:12]=[C:13]([Cl:17])[C:14]([Br:16])=[CH:15][C:4]=2[S:3]1.CO.[OH-].[Na+]>O>[O:1]=[C:2]1[N:6]([CH2:7][C:8]([OH:10])=[O:9])[C:5]2[CH:12]=[C:13]([Cl:17])[C:14]([Br:16])=[CH:15][C:4]=2[S:3]1

Participants

5

Reactant 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 13097126HCID 13097126, compound

Product 1

HCID 130971202-Oxo-5-chloro-6-bromo-3-benzothiazolineacetic acidYield 78.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of methyl 2-oxo-5-chloro-6-bromo-3-benzothiazolineacetate (2.0 g), methanol (250 ml) and 10% sodium hydroxide aqueous solution (2.5 ml) was refluxed with stirring for 1.5 hours and then cooled with ice-water to give crystals, which were separated by filtration. The filtrate was concentrated under reduced pressure to give crystals. The combined crystals were dissolved in water (80 ml) under heating and then insoluble materials were removed by filtration. The filtrate was adjusted at pH 2-3 with 10% hydrochloric acid and cooled to give crystals, which were separated by filtration, washed with water and dried to give crystalline 2-oxo-5-chloro-6-bromo-3-benzothiazolineacetic acid (1.5 g).

Workup

  1. temperaturewas refluxed
  2. customto give crystals, which
  3. customwere separated by filtration
  4. concentrationThe filtrate was concentrated under reduced pressure
  5. customto give crystals
  6. temperatureunder heating
  7. custominsoluble materials were removed by filtration
  8. temperaturecooled
  9. customto give crystals, which
  10. customwere separated by filtration
  11. washwashed with water
  12. customdried

Sources & evidence

ORD record
ord-3104a537ef9d43f699a0624316a89592
Source dataset
uspto-grants-1983_01
Patent number
US04370340

Reaction notes

Loading…