Ethyl Acetate → HCID 66799929, compound

HRID 589679Notes

Reaction equation

HRID 589679 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:4]([C:5]([OH:7])=[O:6])[C:3]=1[OH:11].[Br:12][C:13]1[CH:17]=[C:16]([S:18](Cl)(=[O:20])=[O:19])[S:15][C:14]=1[Cl:22].C([O-])([O-])=O.[Na+].[Na+].CCOC(C)=O>O1CCOCC1.O>[Br:12][C:13]1[CH:17]=[C:16]([S:18]([NH:1][C:2]2[C:3]([OH:11])=[C:4]([CH:8]=[CH:9][CH:10]=2)[C:5]([OH:7])=[O:6])(=[O:20])=[O:19])[S:15][C:14]=1[Cl:22]

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 10340Sodium CarbonateHCID 684433-Aminosalicylic acidHCID 27972204-Bromo-5-chlorothiophene-2-sulfonyl chloride

Product 1

HCID 66799929HCID 66799929, compoundYield 53%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of 3-aminosalicylic acid (0.17 g, 1.11 mmol) and 3-bromo-2-chlorothiophene-5-sulfonyl chloride (0.33 g, 1.11 mmol) in aqueous dioxane (20 mL, 95:5 dioxane/water) was stirred at room temperature for 4 weeks. The pH of the reaction mixture was adjusted to about 9 using 1M Na2CO3 and then EtOAc (200 mL) and water (100 mL) were added. The organic phase was removed and the aqueous phase washed with more EtOAc. The pH of the aqueous phase was adjusted to about 3 with concentrated phosphoric acid and EtOAc (200 mL) was added. The aqueous phase was removed and the organic phase was washed with 1 M HCl and brine, dried over MgSO4, filtered and concentrated. The brown residue was recrystallized from aqueous MeOH at 60° C. The precipitate was collected by filtration and dried over night. The title compound was obtained in 53% yield (0.24 g). 1H NMR (500 MHz, MeOH-d4) δ ppm 6.92 (t, J=7.93 Hz, 1 H) 7.34 (s, 1 H) 7.65 (dd, J=7.93, 1.59 Hz, 1 H) 7.75 (dd, J=7.93, 1.59 Hz, 1 H). MS (ESI+) m/z 412 [M+H]+.

Workup

  1. customThe organic phase was removed
  2. washthe aqueous phase washed with more EtOAc
  3. additionwas added
  4. customThe aqueous phase was removed
  5. washthe organic phase was washed with 1 M HCl and brine
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe brown residue was recrystallized from aqueous MeOH at 60° C
  10. filtrationThe precipitate was collected by filtration
  11. customdried over night

Sources & evidence

ORD record
ord-8d054bc8cac24978a468cb27b04f5876
Source dataset
uspto-grants-2016_01
Patent number
US09233946B2

Reaction notes

Loading…