Dimethylformamide → HCID 54011485, compound

HRID 1856959Notes

Reaction equation

HRID 1856959 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)[CH2:34][CH2:35][CH2:36][CH2:37][CH3:38]>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)[CH2:34][CH2:35][CH2:36][CH2:37][CH3:38]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 125271-IodohexaneHCID 4834830HCID 4834830, compound

Product 1

HCID 54011485HCID 54011485, 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, n-hexyl iodide 0.89 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, and hexane 100 ml was added. 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 0.82 g.

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, and hexane 100 ml
  5. additionwas added
  6. filtrationThe precipitated crystals were filtered
  7. dry with materialdried over phosphorous pentoxide at a temperature of 60° C. for four hours under reduced pressure

Sources & evidence

ORD record
ord-fe3e2836052847cd925f346a877fee29
Source dataset
uspto-grants-2000_11
Patent number
US06143779

Reaction notes

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