Dimethylformamide → HCID 21703281, compound

HRID 363284Notes

Reaction equation

HRID 363284 reaction equation
[C:1]([C:3]([C:20]#[N:21])=[C:4]1[C:16]2[CH:15]=[CH:14][CH:13]=[C:12]([C:17]([OH:19])=[O:18])[C:11]=2[C:10]2[C:5]1=[CH:6][CH:7]=[CH:8][CH:9]=2)#[N:2].CN(C)C=O.[CH:27]([C:29]1[CH:36]=[CH:35][C:32](CCl)=[CH:31][CH:30]=1)=[CH2:28].[C:37](=O)(O)[O-].[Na+]>O>[C:20]([C:3]([C:1]#[N:2])=[C:4]1[C:16]2[CH:15]=[CH:14][CH:13]=[C:12]([C:17]([O:19][CH:27]([CH:28]=[CH2:37])[C:29]3[CH:30]=[CH:31][CH:32]=[CH:35][CH:36]=3)=[O:18])[C:11]=2[C:10]2[C:5]1=[CH:6][CH:7]=[CH:8][CH:9]=2)#[N:21]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 74126p-Vinylbenzyl chlorideHCID 516892Sodium BicarbonateHCID 220351399-(Dicyanomethylidene)-9H-fluorene-4-carboxylic acid

Product 1

HCID 21703281HCID 21703281, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
40 °C

Procedure

To a 1 liter round bottomed flask were added 60.0 grams of 9-dicyanomethylenefluorene-4-carboxylic acid, 700 milliliters of N,N-dimethylformamide, 67.1 grams of 4-vinylbenzyl chloride, and 37.0 grams of sodium bicarbonate, and the resulting mixture was stirred at 40° C. for 48 hours. The mixture was poured into 1,500 milliliters of distilled water with vigorous stirring, and the resulting aqueous mixture was extracted with 1,000 milliliters of dichloromethane. The organic layer was separated and was further washed with 1,500 milliliters of distilled water and dried over anhydrous magnesium sulfate. Subsequently, the organic solvent was removed by means of a rotary evaporator and the residue was recrystallized from a mixture of dichloromethane and methanol (2:1 by volume) to give vinylbenzyl 9-dicyanomethylenefluorene-4-carboxylate after filtration and drying in a vacuo for 48 hours.

Workup

  1. extractionthe resulting aqueous mixture was extracted with 1,000 milliliters of dichloromethane
  2. customThe organic layer was separated
  3. washwas further washed with 1,500 milliliters of distilled water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customSubsequently, the organic solvent was removed by means of a rotary evaporator
  6. customthe residue was recrystallized from a mixture of dichloromethane and methanol (2:1 by volume)

Sources & evidence

ORD record
ord-553ee59cea134c9b816c74a82daf67ab
Source dataset
uspto-grants-1999_02
Patent number
US05874193

Reaction notes

Loading…