Hydrochloric Acid → HCID 71715287, compound

HRID 2205427Notes

Reaction equation

HRID 2205427 reaction equation
[CH2:1]([N:8]1[C:12](=[O:13])[N:11]([CH2:14][CH2:15][O:16]C(=O)C2C=CC=CC=2)[C:10](=[O:25])[S:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.C(OCC)(=O)C>CO>[CH2:1]([N:8]1[C:12](=[O:13])[N:11]([CH2:14][CH2:15][OH:16])[C:10](=[O:25])[S:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 89772217HCID 89772217, compound

Product 1

HCID 71715287HCID 71715287, compoundYield 81.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

To a suspension of benzoic acid 2-(2-benzyl-3,5-dioxo-[1,2,4]thiadiazolidin-4-yl)ethyl ester (74.0 g, 207.6 mmol) in methanol (740 mL) 12N HCl (740 mL) was added at room temperature. The mixture was heated at 50° C. for 18 h, then additional 12N HCl (250 mL) was added and the mixture was stirred for 84 hours at 40° C. until hydrolysis was completed. The mixture was concentrated at reduced pressure to remove the methanol, and the resulting mixture was extracted with methylene chloride (3×500 mL). The combined organic layers were dried (Na2SO4), filtered and evaporated to yield an oil that was treated with hot ethyl acetate (200 mL) and precipitated by the addition of n-heptane (200 mL) to yield the pure desired product as a white solid (42.5 g, 81%)

Workup

  1. additionwas added at room temperature
  2. concentrationThe mixture was concentrated at reduced pressure
  3. customto remove the methanol
  4. extractionthe resulting mixture was extracted with methylene chloride (3×500 mL)
  5. dry with materialThe combined organic layers were dried (Na2SO4)
  6. filtrationfiltered
  7. customevaporated
  8. customto yield an oil that
  9. customprecipitated by the addition of n-heptane (200 mL)

Sources & evidence

ORD record
ord-c7d303d987b84c44b11bcf4bef06cadf
Source dataset
uspto-grants-2016_06
Patent number
US09371299B2

Reaction notes

Loading…