Diethyl Malonate → HCID 23303048, compound

HRID 2289599Notes

Reaction equation

HRID 2289599 reaction equation
Br[C:2]1[N:9]2[C:5](=[N:6][C:7]3[CH:13]=[CH:12][CH:11]=[CH:10][C:8]=32)[S:4][N:3]=1.[C:14]([O:22][CH2:23][CH3:24])(=[O:21])[CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17].C(N(CC)CC)C>C1COCC1>[CH2:23]([O:22][C:14]([CH:15]([C:16]([O:18][CH2:19][CH3:20])=[O:17])[C:2]1[N:9]2[C:5](=[N:6][C:7]3[CH:13]=[CH:12][CH:11]=[CH:10][C:8]=32)[S:4][N:3]=1)=[O:21])[CH3:24]

Participants

5

Reactant 3

HCID 7761Diethyl MalonateHCID 8471TriethylamineHCID 10198942HCID 10198942, compound

Product 1

HCID 23303048HCID 23303048, compoundYield 54%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 3-bromo-1,2,4-thiadiazolo[4,5-a]benzimidazole (0.2 g, 0.78 mmole), diethyl malonate (0.15 g, 0.94 mmol) and triethylamine (0.13 mL, 0.94 mmole) in 8 mL of THF was refluxed under a nitrogen atmosphere for 36 h. The resulting mixture was extracted with ethyl acetate, washed with water and 10% aqueous sodium sulfate. The organic layer was dried over magnesium sulfate to give the crude product, which was purified by flash chromatography (35% ethyl acetate:65%. hexane) to afford 0.14 g (54%) of the title compound as a yellow oil:

Workup

  1. temperaturewas refluxed under a nitrogen atmosphere for 36 h
  2. extractionThe resulting mixture was extracted with ethyl acetate
  3. washwashed with water and 10% aqueous sodium sulfate
  4. dry with materialThe organic layer was dried over magnesium sulfate
  5. customto give the crude product, which
  6. customwas purified by flash chromatography (35% ethyl acetate:65%. hexane)

Sources & evidence

ORD record
ord-347629714eaa408292668d0908795210
Source dataset
uspto-grants-2000_07
Patent number
US06093738

Reaction notes

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