Potassium Carbonate → HCID 19813444, compound

HRID 467107Notes

Reaction equation

HRID 467107 reaction equation
Cl[CH2:2][C:3]1[S:7][C:6]2[CH:8]=[CH:9][C:10]([N+:12]([O-:14])=[O:13])=[CH:11][C:5]=2[CH:4]=1.[CH3:15][NH:16][CH2:17][CH2:18][C:19]1[CH:24]=[CH:23][C:22]([N+:25]([O-:27])=[O:26])=[CH:21][CH:20]=1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[CH3:15][N:16]([CH2:17][CH2:18][C:19]1[CH:24]=[CH:23][C:22]([N+:25]([O-:27])=[O:26])=[CH:21][CH:20]=1)[CH2:2][C:3]1[S:7][C:6]2[CH:8]=[CH:9][C:10]([N+:12]([O-:14])=[O:13])=[CH:11][C:5]=2[CH:4]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 2794239N-methyl-4-nitrophenethylamineHCID 151337582-(Chloromethyl)-5-nitro-1-benzothiophene

Product 1

HCID 19813444HCID 19813444, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of the product of part (A) above (3.20 g), N-methyl-4-nitrophenethylamine (2.52 g), anhydrous potassium carbonate (4.0 g) and acetonitrile (40 ml) was heated under reflux with stirring for 20 hours and then cooled and filtered. The residue was washed with acetonitrile, and the combined filtrate and washings were evaporated to give an oil which was chromatographed on silica gel. Elution with dichloromethane first gave impurity followed by pure product. The product-containing fractions were evaporated to give the title compound (4.17 g), m.p. 76°-78° (from isopropanol).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux
  3. temperaturecooled
  4. filtrationfiltered
  5. washThe residue was washed with acetonitrile
  6. customthe combined filtrate and washings were evaporated
  7. customto give an oil which
  8. customwas chromatographed on silica gel
  9. washElution with dichloromethane first gave impurity
  10. customThe product-containing fractions were evaporated

Sources & evidence

ORD record
ord-58cea7dae8a64416a31f76c3394f5fee
Source dataset
uspto-grants-1992_10
Patent number
US05158964

Reaction notes

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