Diethyl Ether → HCID 54370108, compound

HRID 1638460Notes

Reaction equation

HRID 1638460 reaction equation
[H-].[Na+].[CH3:3][N:4]([CH:6]=[C:7]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[NH:9][C:8]1=[O:16])[CH3:5].I[C:18]1[CH:19]=[C:20]([O:24][CH3:25])[CH:21]=[CH:22][CH:23]=1.CCOCC>CCCCCC.CN(C)C=O>[CH3:25][O:24][C:20]1[CH:19]=[C:18]([N:9]2[C:10]3[C:15](=[CH:14][CH:13]=[CH:12][CH:11]=3)[C:7](=[CH:6][N:4]([CH3:3])[CH3:5])[C:8]2=[O:16])[CH:23]=[CH:22][CH:21]=1

Participants

7

Reactant 4

HCID 3283Diethyl EtherHCID 24758Sodium hydrideHCID 69839Benzene, 1-iodo-3-methoxy-HCID 30289742H-Indol-2-one, 3-[(dimethylamino)methylene]-1,3-dihydro-, (Z)-

Product 1

HCID 54370108HCID 54370108, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×HCID 8058HexaneSolvent

Procedure

In a flame dried flask under nitrogen, sodium hydride (50% dispersion in oil, 0.96 g, 20 mmoles) was washed free of oil with hexane. Dry dimethylformamide (DMF, 50 ml) and 3-(dimethylaminomethylene)-2(1H,3H)-indolone [Chem. Ber. 85:774 (1952); 3.77 g, 20 mmoles] were added, and the mixture stirred for 30 minutes (until gas evolution ceased), m-Iodoanisole (9.36 g, 40 mmoles) in 20 ml DMF was added, followed by Cu2Br2 (5.74 g, 20 mmoles). The reaction mixture was heated at 120°-130° for 40 hours, poured over 300 g of ice, stirred with 300 ml ether, filtered and the ether layer separated, dried over MgSO4, filtered and concentrated to an oil. The oil was chromatographed on silica gel, using ethyl acetate as eluant and title product initially isolated as an oil, crystallized from ether, 2.46 g (42%), m.p. 106°-108.5° (dec.).

Workup

  1. customIn a flame dried flask under nitrogen
  2. additionwas added
  3. temperatureThe reaction mixture was heated at 120°-130° for 40 hours
  4. filtrationfiltered
  5. customthe ether layer separated
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated to an oil
  9. customThe oil was chromatographed on silica gel

Sources & evidence

ORD record
ord-504619a6bd1b4bfcb6e4dcf336ccf088
Source dataset
uspto-grants-1989_11
Patent number
US04879391

Reaction notes

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