Oxalyl chloride → NSC 25351

HRID 2242463Notes

Reaction equation

HRID 2242463 reaction equation
[CH:1]1[CH:14]=[C:13]2[C:4]([CH:5]3[C:16]([C:17](O)=[O:18])=[C:15]([C:20]([OH:22])=[O:21])[CH:12]2[C:11]2[C:6]3=[CH:7][CH:8]=[CH:9][CH:10]=2)=[CH:3][CH:2]=1.C(Cl)(=O)C(Cl)=O>ClCCl.CN(C)C=O>[CH:9]1[CH:10]=[C:11]2[C:6]([CH:5]3[C:16]4[C:17]([O:22][C:20](=[O:21])[C:15]=4[CH:12]2[C:13]2[C:4]3=[CH:3][CH:2]=[CH:1][CH:14]=2)=[O:18])=[CH:7][CH:8]=1

Participants

5

Reactant 2

HCID 65578Oxalyl chloride2×HCID 2289069,10-Ethenoanthracene-11,12-dicarboxylic acid, 9,10-dihydro-

Product 1

HCID 230439NSC 25351Yield 92.5%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

As shown in FIG. 2A, diacid 2 (8.76 g, 29.2 mmol) was suspended in dry dichloromethane (ca. 300 mL) in a dry, septum-capped round-bottom flask, to which was added a few drops of dry dimethylformamide. The mixture was cooled to 0° C. in an ice-water bath and the flask was connected to a oil-bubbler with flexible plastic tubing. Oxalyl chloride (3.9 g, 30.7 mmol) was added dropwise with a syringe as the suspension was stirred. Within few minutes, gas was released through the oil bubbler as the reaction began. The reaction mixture was adequately cooled prior to the addition of oxalyl chloride to avoid a violent release of gas. The reaction mixture was allowed to warm to room temperature as it was stirred overnight (ca. 16 h), during which the reaction mixture became homogeneous. The solvent was evaporated under vacuum and the resulting crude product was recrystallized from toluene to give the title compound as pale beige crystals (7.41 g, 90%). 1H NMR (500 MHz, CDCl3): 7.45 (4H, dd, J=5.2 and 3.2 Hz), 7.09 (4H, dd, J=5.0 and 3.5 Hz), 5.55 (2H, s).

Workup

  1. customseptum-capped round-bottom flask
  2. waitWithin few minutes
  3. temperatureThe reaction mixture was adequately cooled
  4. temperatureto warm to room temperature as it
  5. stirringwas stirred overnight (ca. 16 h)
  6. customThe solvent was evaporated under vacuum
  7. customthe resulting crude product was recrystallized from toluene

Sources & evidence

ORD record
ord-f570620e61ef4ff78e7fc4df3e0b0c21
Source dataset
uspto-grants-2010_03
Patent number
US07671166B2

Reaction notes

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