Sodium Carbonate → HCID 21463486, compound

HRID 1940594Notes

Reaction equation

HRID 1940594 reaction equation
[NH2:1][C:2]1[C:10]2[O:9][CH2:8][CH2:7][C:6]=2[CH:5]=[C:4]([N+:11]([O-:13])=[O:12])[CH:3]=1.Cl.[CH3:15][N:16]([CH3:20])[CH2:17][CH2:18]Cl.C(=O)([O-])[O-].[Na+].[Na+]>C(O)C>[CH3:15][N:16]([CH3:20])[CH2:17][CH2:18][NH:1][C:2]1[C:10]2[O:9][CH2:8][CH2:7][C:6]=2[CH:5]=[C:4]([N+:11]([O-:13])=[O:12])[CH:3]=1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 11636816N,N-Dimethylaminoethyl chloride hydrochlorideHCID 21463488HCID 21463488, compound

Product 1

HCID 21463486HCID 21463486, compoundYield 15%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 7-amino-5-nitro-2,3-dihydrobenzofuran (D4) (2 g) in ethanol (60 ml) was treated with 2-dimethylaminoethyl chloride hydrochloride (3.36 g) and excess sodium carbonate (6 g), and heated at reflux for 4 days under argon. The solvent was evaporated under reduced pressure, and the residue partitioned between water and chloroform. The organic phase was dried (Na2SO4) and evaporated under reduced pressure to leave an oil which was chromatographed on silica, eluting with methanol and chloroform to give the title compound as a viscous red oil (416 mg, 15%)

Workup

  1. temperatureheated
  2. temperatureat reflux for 4 days under argon
  3. customThe solvent was evaporated under reduced pressure
  4. customthe residue partitioned between water and chloroform
  5. dry with materialThe organic phase was dried (Na2SO4)
  6. customevaporated under reduced pressure
  7. customto leave an oil which
  8. customwas chromatographed on silica
  9. washeluting with methanol and chloroform

Sources & evidence

ORD record
ord-2ba7ffd4f1db48af8b719b65808e2445
Source dataset
uspto-grants-1997_12
Patent number
US05700818

Reaction notes

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