Dimethylformamide → HCID 12926028, compound

HRID 894628Notes

Reaction equation

HRID 894628 reaction equation
NC1[C:7]2[O:8][C:9]3([C:12](=[O:13])[C:6]=2[CH:5]=[CH:4][CH:3]=1)[CH2:11][CH2:10]3.[CH2:14](Br)[CH3:15].[C:17](=O)([O-])O.[Na+].[CH3:22][N:23]([CH3:26])C=O>O>[CH2:26]([N:23]([CH2:14][CH3:15])[C:22]1[C:7]2[O:8][C:9]3([C:12](=[O:13])[C:6]=2[CH:5]=[CH:4][CH:3]=1)[CH2:11][CH2:10]3)[CH3:17]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 6332Ethyl BromideHCID 516892Sodium BicarbonateHCID 12925993HCID 12925993, compound

Product 1

HCID 12926028HCID 12926028, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 7-aminospiro[benzo[b]furan-2(3H),1'-cyclopropane]-3-one (1.75 g.) and ethylbromide (5.45 g.) and sodium hydrogen carbonate (1.68 g.) in N,N-dimethylformamide (50 ml.) was heated at 100° C. for 4 hours. The reaction mixture was diluted with water and extracted with ethyl acetate. The extract was washed with water and dried, then the solvent was evaporated off. The residue was subjected to column-chromatography on silica-gel. The first fraction eluted with hexane-ethyl acetate (97:3) was recrystallized from ethanol to give 7-diethylaminospiro[benzo[b]furan-2(3H),1'-cyclopropane]-3-one (0.801 g.) as yellow needles melting at 39.3° C.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe extract was washed with water
  3. customdried
  4. customthe solvent was evaporated off
  5. washThe first fraction eluted with hexane-ethyl acetate (97:3)
  6. customwas recrystallized from ethanol

Sources & evidence

ORD record
ord-8e6ed9fb2a9d4a3594f297ae47b62272
Source dataset
uspto-grants-1981_08
Patent number
US04284644

Reaction notes

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