Acetic Acid → HCID 19940142, compound

HRID 1654597Notes

Reaction equation

HRID 1654597 reaction equation
C=O.[C:3](O)(=O)C.[CH2:7]([NH:10][CH2:11][CH:12]=[CH2:13])[CH:8]=[CH2:9].[S:14]1[CH:18]=[CH:17][CH:16]=[C:15]1[C:19]1[NH:20][C:21]([C:24]2[S:25][CH:26]=[CH:27][CH:28]=2)=[CH:22][CH:23]=1>C(O)C>[CH2:7]([N:10]([CH2:3][C:22]1[CH:23]=[C:19]([C:15]2[S:14][CH:18]=[CH:17][CH:16]=2)[NH:20][C:21]=1[C:24]1[S:25][CH:26]=[CH:27][CH:28]=1)[CH2:11][CH:12]=[CH2:13])[CH:8]=[CH2:9]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 712FormaldehydeHCID 31279DiallylamineHCID 41751102,5-Di(thiophen-2-yl)-1H-pyrrole

Product 1

HCID 19940142HCID 19940142, compoundYield 65.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Paraformaldehyde (9.1 mg, 0.3 mmol) was added to a solution of acetic acid (0.33 mL, 0.71 mmol) and diallylamine (0.32 mmol) in 1 mL of ethanol. After stirring at room temperature for a few minutes, 2.5-dithienylpyrrole (0.3 mmol) was then added all at once. The reaction mixture was then allowed to stir at 60° for 19 hours. The reaction solvent was evaporated under reduced pressure, and the crude product was taken up with ethyl acetate. The organic layer was then washed with water (10 mL) and brine (10 mL). The aqueous layer was extracted with chloroform (10 mL). The combined organic layers were then dried over anhydrous magnesium sulfate, filtered and the solvent was removed under pressure. The crude product was purified on 50 g of silica gel. Elution with hexane-ethyl acetate (5:1), gave 67 mg (65%) of title compound.

Workup

  1. stirringto stir at 60° for 19 hours
  2. customThe reaction solvent was evaporated under reduced pressure
  3. washThe organic layer was then washed with water (10 mL) and brine (10 mL)
  4. extractionThe aqueous layer was extracted with chloroform (10 mL)
  5. dry with materialThe combined organic layers were then dried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. customthe solvent was removed under pressure
  8. customThe crude product was purified on 50 g of silica gel
  9. washElution with hexane-ethyl acetate (5:1)

Sources & evidence

ORD record
ord-bca377bd25144c2ba40f734eee1f295a
Source dataset
uspto-grants-1995_04
Patent number
USRE034919

Reaction notes

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