3,4-Bis(benzyloxy)benzaldehyde → HCID 3010537, compound

HRID 2213576Notes

Reaction equation

HRID 2213576 reaction equation
[S:1]1[CH2:7][C:5](=[O:6])[N:4]([CH2:8][C:9]([OH:11])=[O:10])[C:2]1=[S:3].[CH2:12]([O:19][C:20]1[CH:21]=[C:22]([CH:25]=[CH:26][C:27]=1[O:28][CH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)[CH:23]=O)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C([O-])(=O)C.[Na+]>C(O)(=O)C.O>[C:13]1([CH2:12][O:19][C:20]2[CH:21]=[C:22]([CH:23]=[C:7]3[S:1][C:2](=[S:3])[N:4]([CH2:8][C:9]([OH:11])=[O:10])[C:5]3=[O:6])[CH:25]=[CH:26][C:27]=2[O:28][CH2:29][C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

6

Reactant 3

HCID 795263,4-Bis(benzyloxy)benzaldehydeHCID 797933-Thiazolidineacetic acid, 4-oxo-2-thioxo-HCID 517045Sodium Acetate

Product 1

HCID 3010537HCID 3010537, compoundYield 82.2%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

A solution of rhodanine-3-acetic acid (1 g, 5.20 mmol, 1 eq), 3,4-dibenzyloxybenzaldehyde (2.04 g, 6.25 mmol, 1.2 eq), and sodium acetate (1.3 g, 15.6 mmol, 3 eq) in acetic acid (30 ml) was heated to reflux, and stirred overnight. As the reaction mixture cooled to room temperature the product precipitated and it was filtered and washed with acetic acid, then petroleum ether. The gummy solid was dissolved in ethyl acetate (20 mL) and extracted into saturated aqueous sodium bicarbonate (2×30 mL). The basic extracts were combined, washed with ethyl acetate, and acidified to pH 1 with concentrated HCl. The aqueous solution was extracted with ethyl acetate (2×10 mL), and the organic extracts combined, dried over sodium sulfate and evaporated in vacuo. Recrystallization from ethyl acetate and petroleum ether gave the product which was suspended in water and freeze-dried overnight in vacuo to give the product as a fluffy yellow powder (2.1 g, 81%). mp 235–238° C.: 1H NMR (d6 DMSO) δ 7.79 (s, 1H, C═C—H), 5.25 (s, 2H, CH2Ph), 5.23 (s, 2H, CH2Ph), 4.73 (s, 2H, CH2CO2H). Anal. Found: C, 63.53; H, 4.31; N, 2.85; S, 13.05. Calcd for C26H21NO5S2: C, 63.39; H, 4.21; N, 2.84; S, 12.92.

Workup

  1. temperatureto reflux
  2. customprecipitated
  3. filtrationit was filtered
  4. washwashed with acetic acid
  5. dissolutionThe gummy solid was dissolved in ethyl acetate (20 mL)
  6. extractionextracted into saturated aqueous sodium bicarbonate (2×30 mL)
  7. washwashed with ethyl acetate
  8. extractionThe aqueous solution was extracted with ethyl acetate (2×10 mL)
  9. dry with materialdried over sodium sulfate
  10. customevaporated in vacuo
  11. customRecrystallization from ethyl acetate and petroleum ether
  12. customgave the product which
  13. customfreeze-dried overnight in vacuo

Sources & evidence

ORD record
ord-c4ee8c6a6e8e4acfab75f2f652af2587
Source dataset
uspto-grants-2006_09
Patent number
US07105554B2

Reaction notes

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