Water → HCID 70200075, compound

HRID 342429Notes

Reaction equation

HRID 342429 reaction equation
[H-].[Na+].[C:3]([NH:6][C:7]1[C:8]2[CH:16]=[CH:15][CH:14]=[C:13]([N+:17]([O-:19])=[O:18])[C:9]=2[O:10][C:11]=1[CH3:12])(=[O:5])[CH3:4].I[CH2:21][CH3:22].O>CN(C)C=O>[C:3]([N:6]([C:7]1[C:8]2[CH:16]=[CH:15][CH:14]=[C:13]([N+:17]([O-:19])=[O:18])[C:9]=2[O:10][C:11]=1[CH3:12])[CH2:21][CH3:22])(=[O:5])[CH3:4]

Participants

6

Reactant 4

HCID 962WaterHCID 6340IodoethaneHCID 24758Sodium hydrideHCID 70200165HCID 70200165, compound

Product 1

HCID 70200075HCID 70200075, compoundYield 98.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Sodium hydride (60%, 54 mg) was added to a solution of 3-acetylamino-2-methyl-7-nitrobenzo[b]furan (280 mg) in N,N-dimethylformamide (3 ml) at 4° C. The mixture was stirred for 30 minutes and to the mixture was added iodoethane (240 mg). The mixture was stirred at ambient temperature for 2 hours. The reaction mixture was poured into cold water and the separated oil was extracted with ethyl acetate. The extract was washed with brine, dried over sodium sulfate and concentrated in vacuo. The residue was purified by column chromatography on silica gel to give 3-(N-acetyl-N-ethylamino)-2-methyl-7-nitrobenzo[b]furan as a crystalline solid (310 mg).

Workup

  1. stirringThe mixture was stirred at ambient temperature for 2 hours
  2. extractionthe separated oil was extracted with ethyl acetate
  3. washThe extract was washed with brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-b63be30bf23a475882ff2af6859a8b56
Source dataset
uspto-grants-1999_01
Patent number
US05858995

Reaction notes

Loading…