Hydrochloric Acid → Thioflavin

HRID 2292103Notes

Reaction equation

HRID 2292103 reaction equation
O1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:4](=[S:5])[CH2:3][CH:2]1[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.Cl>C(O)(=O)C.[Zn]>[S:5]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH2:2][CH2:3][CH:4]1[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 86742684HCID 86742684, compound

Product 1

HCID 22251ThioflavinYield 27.1%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 176Acetic AcidSolvent

Procedure

Thioflavanone (10.0 g) was dissolved in acetic acid (300 ml) and concentrated hydrochloric acid (30 ml) and added to zinc amalgam prepared from zinc powder (100 g.) and mercuric chloride (8.0 g.) The reaction mixture was stirred at room temperature for 3 hr., then allowed to stand overnight. The reaction mixture was filtered and the filtrate diluted with water and extracted with toluene. The toluene extract was washed with water, dried and evaporated. Trituration of the residue with ethanol gave, on filtration, thioflavan (2.55 g) m.pt. 45°-49°-Recrystallisation of a sample from ethanol gave pure thioflavan m.pt 55°-56°.

Workup

  1. waitto stand overnight
  2. filtrationThe reaction mixture was filtered
  3. additionthe filtrate diluted with water
  4. extractionextracted with toluene
  5. extractionThe toluene extract
  6. washwas washed with water
  7. customdried
  8. customevaporated

Sources & evidence

ORD record
ord-6c8c8fb0a95440dd8773be69647f6d5a
Source dataset
uspto-grants-1989_01
Patent number
US04801593

Reaction notes

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