Hydrochloric Acid → HCID 11322143, compound

HRID 972486Notes

Reaction equation

HRID 972486 reaction equation
N([O-])=O.[Na+].N[C:6]1[CH:11]=[CH:10][C:9]([C:12](=[O:14])[CH3:13])=[CH:8][CH:7]=1.Cl.[S:16]1[CH:20]=[CH:19][CH:18]=[C:17]1[CH:21]=[CH:22]C(O)=O.C([O-])(=O)C.[Na+]>O.CC(C)=O>[C:12]([C:9]1[CH:10]=[CH:11][C:6](/[CH:22]=[CH:21]/[C:17]2[S:16][CH:20]=[CH:19][CH:18]=2)=[CH:7][CH:8]=1)(=[O:14])[CH3:13]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 7468p-AminoacetophenoneHCID 928683-Thiophen-2-ylprop-2-enoic acidHCID 517045Sodium AcetateHCID 23668193Sodium Nitrite

Product 1

HCID 11322143HCID 11322143, compoundYield 54.9%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent3×

Procedure

9.3 g of sodium nitrite dissolved in the minimum amount of water was added to a mixture of 18.18 g of p-amino-acetophenone, 36 ml of concentrated hydrochloric acid and 36 g of water, and the resulting mixture was ice-cooled and diazotized while stirring. To the diazotized solution was added 127 cc of a solution of 16.9 g of β-2-thienylacrylic acid in acetone. An aqueous solution of 25.4 g of sodium acetate dissolved in 10 ml of water and 5.6 g of cupric chloride were then added to the mixture whereby a gas evolved and the reaction proceeded. After the reaction mixture was stirred for 24 hours while cooling, the acetone was distilled off and the residue was extracted with benzene. The benzene layer was shaken with a 5% aqueous sodium hydroxide solution, washed with water and dried over Na2SO4. The drying agent used was filtered out and the solvent was distilled off. The resulting residue was purified by column chromatography on alumina using benzene as a developing solvent to obtain 13.73 g of (E)-2-(4-acetylstyryl)thiophene in a 50% yield. The melting point of the product after recrystallization from benzene was 130° to 131° C.

Workup

  1. temperaturecooled
  2. stirringAfter the reaction mixture was stirred for 24 hours
  3. temperaturewhile cooling
  4. distillationthe acetone was distilled off
  5. extractionthe residue was extracted with benzene
  6. stirringThe benzene layer was shaken with a 5% aqueous sodium hydroxide solution
  7. washwashed with water
  8. dry with materialdried over Na2SO4
  9. filtrationThe drying agent used was filtered out
  10. distillationthe solvent was distilled off
  11. customThe resulting residue was purified by column chromatography on alumina

Sources & evidence

ORD record
ord-3b8f97be901b42128d937cdd54c3adce
Source dataset
uspto-grants-1977_10
Patent number
US04053466

Reaction notes

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