Dimethylformamide → HCID 4892113, compound

HRID 1856955Notes

Reaction equation

HRID 1856955 reaction equation
[OH:1][C:2]1[CH:21]=[CH:20][C:5]2[C:6](=[O:19])[C:7](=[CH:9][C:10]3[CH:18]=[CH:17][C:16]4[O:15][CH2:14][O:13][C:12]=4[CH:11]=3)[O:8][C:4]=2[CH:3]=1.C(=O)([O-])[O-].[K+].[K+].CN(C)C=O.[CH2:33](I)[CH3:34]>C(OCC)(=O)C>[CH2:33]([O:1][C:2]1[CH:21]=[CH:20][C:5]2[C:6](=[O:19])[C:7](=[CH:9][C:10]3[CH:18]=[CH:17][C:16]4[O:15][CH2:14][O:13][C:12]=4[CH:11]=3)[O:8][C:4]=2[CH:3]=1)[CH3:34]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 6340IodoethaneHCID 11430Potassium CarbonateHCID 4834830HCID 4834830, compound

Product 1

HCID 4892113HCID 4892113, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

After 6-hydroxy-2-piperonylidene-3(2H)-benzofuranone 1 g and potassium carbonate 1.95 g were added to dimethylformamide 10 ml, ethyl iodide 0.48 ml was added, and the mixture was reacted at a temperature of 100° C. for two hours. After the solution was cooled to room temperature, ethyl acetate 200 ml was added. The ethyl acetate solution was washed with water 100 ml twice and a saturated sodium chloride solution 50 ml twice. The ethyl acetate solution was dehydrated with anhydrous magnesium sulfate, and concentrated to 40 ml under reduced pressure. The precipitated crystals were filtered and dried over phosphorous pentoxide at a temperature of 60° C. for four hours under reduced pressure to obtain the desired compound 0.65 g. FAB MASS; 311 (M+1) 1H-NMR (ppm, in CDCl3); 1.45 (3H, t), 4.10 (2H, q), 6.00 (2H, s), 6.68-6.70 (3H, m), 6.82 (1H, d, J=7.9 Hz), 7.24 (1H, dd, J=8.2 Hz), 7.49 (1H, d, J=1.5 Hz), 7.63 (1H, d, J=8.2 Hz)

Workup

  1. additionwas added
  2. customthe mixture was reacted at a temperature of 100° C. for two hours
  3. washThe ethyl acetate solution was washed with water 100 ml twice
  4. concentrationconcentrated to 40 ml under reduced pressure
  5. filtrationThe precipitated crystals were filtered
  6. dry with materialdried over phosphorous pentoxide at a temperature of 60° C. for four hours under reduced pressure

Sources & evidence

ORD record
ord-e8fa138aa1c64f999e759fb6ba70c538
Source dataset
uspto-grants-2000_11
Patent number
US06143779

Reaction notes

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