Dimethylformamide → HCID 89619455, compound

HRID 591217Notes

Reaction equation

HRID 591217 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4](C(C(O)=O)C(O)=O)[CH:5]=[C:6]([Cl:8])[CH:7]=1.Cl[CH2:17][Cl:18].[C:19](Cl)(=O)[C:20]([Cl:22])=[O:21].CN(C)C=[O:28]>>[Cl:1][C:2]1[CH:3]=[C:4]([CH:19]([C:17]([Cl:18])=[O:28])[C:20]([Cl:22])=[O:21])[CH:5]=[C:6]([Cl:8])[CH:7]=1

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 6344DichloromethaneHCID 65578Oxalyl chlorideHCID 73554943HCID 73554943, compound

Product 1

HCID 89619455HCID 89619455, compound

Procedure

A 4-necked 500-mL flask equipped with overhead stirrer, condenser, thermometer, and addition funnel was charged with 2-(3,5-dichlorophenyl)propanedioic acid (21.8 g, 87.6 mmol), anhydrous dichloromethane (300 mL), and N,N-dimethylformamide (0.1 mL). To this stirred solution was added oxalyl chloride (19 mL, 217 mmol) over 10 min at room temperature. The mixture was stirred at room temperature for 1 hr, then refluxed for 2.5 h under nitrogen. The resulting yellow solution was concentrated under reduced pressure (20 mmHg) at a temperature of 25° C. to yield the crude product as an orange oil. The resulting material was used directly in the next step.

Workup

  1. customA 4-necked 500-mL flask equipped with overhead stirrer, condenser
  2. additionthermometer, and addition funnel
  3. temperaturerefluxed for 2.5 h under nitrogen
  4. concentrationThe resulting yellow solution was concentrated under reduced pressure (20 mmHg) at a temperature of 25° C.

Sources & evidence

ORD record
ord-fccbe3c0aaf44316a48bea01e22bc420
Source dataset
uspto-grants-2016_01
Patent number
US09238650B2

Reaction notes

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