HCID 72644370, compound → HCID 72644365, compound

HRID 1581644Notes

Reaction equation

HRID 1581644 reaction equation
CS[CH:3]([C:9]1[CH:14]=[C:13]([CH:15]=[C:16]2[S:20][C:19](=[O:21])[NH:18][C:17]2=[O:22])[CH:12]=[CH:11][C:10]=1[O:23][CH3:24])[C:4]([O:6][CH2:7][CH3:8])=[O:5]>[Zn].C(O)(=O)C>[O:21]=[C:19]1[NH:18][C:17](=[O:22])[C:16](=[CH:15][C:13]2[CH:12]=[CH:11][C:10]([O:23][CH3:24])=[C:9]([CH2:3][C:4]([O:6][CH2:7][CH3:8])=[O:5])[CH:14]=2)[S:20]1

Participants

4

Reactant 1

HCID 72644370HCID 72644370, compound

Product 1

HCID 72644365HCID 72644365, compoundYield 50.2%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 176Acetic AcidSolvent

Procedure

Ethyl 2-methylthio-2-[5-[(2,4-dioxothiazolidin-5-ylidene)methyl]-2-methoxyphenyl]acetate (6.18 g, 16.8 mmol) and acetic acid (100 mL) were mixed, and zinc powder (46.0 g, 706 mmol) was added under stirring, which was stirred for 24 hours at room temperature. Zinc was collected by filtration. washed with acetic acid, and the filtrate was concentrated. The residue was dissolved into ethyl acetate, washed with water and brine in sequence, then dried over anhydrous sodium sulfate and concentrated. The residue was recrystallized from methanol to obtain 2.71 g (50%) of the title compound as yellow powder.

Workup

  1. stirringwhich was stirred for 24 hours at room temperature
  2. filtrationZinc was collected by filtration
  3. washwashed with acetic acid
  4. concentrationthe filtrate was concentrated
  5. dissolutionThe residue was dissolved into ethyl acetate
  6. washwashed with water and brine in sequence
  7. dry with materialdried over anhydrous sodium sulfate
  8. concentrationconcentrated
  9. customThe residue was recrystallized from methanol

Sources & evidence

ORD record
ord-b36b050e7f6c408e86b70ed8f9e10a34
Source dataset
uspto-grants-2004_05
Patent number
US06730687B1

Reaction notes

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