Potassium Carbonate → HCID 19813444, compound

HRID 1031986Notes

Reaction equation

HRID 1031986 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 wit acetonitrile, and the combined filtrate and washings were evaporated to give an oil which was chromarographed 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 wit acetonitrile
  6. customthe combined filtrate and washings were evaporated
  7. customto give an oil which
  8. washElution with dichloromethane first gave impurity
  9. customThe product-containing fractions were evaporated

Sources & evidence

ORD record
ord-ca0330d59e734aefaa0f924b149c36e1
Source dataset
uspto-grants-1990_09
Patent number
US04956382

Reaction notes

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