Sodium Carbonate → HCID 67517443, compound

HRID 1519508Notes

Reaction equation

HRID 1519508 reaction equation
[O:1]=[C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4](=[O:11])[N:3]1[C:12]1[CH:13]=[C:14]([CH2:18][C:19](O)=[O:20])[CH:15]=[CH:16][CH:17]=1.[C:22](Cl)(=O)[C:23](Cl)=O.[Cl-].[Al+3].[Cl-].[Cl-].C(=O)([O-])[O-].[Na+].[Na+]>C(Cl)Cl.CN(C=O)C>[O:20]=[C:19]1[CH2:18][C:14]2[CH:13]=[C:12]([N:3]3[C:2](=[O:1])[C:10]4[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=4)[C:4]3=[O:11])[CH:17]=[CH:16][C:15]=2[CH2:23][CH2:22]1

Participants

7

Reactant 4

HCID 10340Sodium CarbonateHCID 65578Oxalyl chlorideHCID 6451240Aluminum(III) ChlorideHCID 212622833-(1,3-Dihydro-1,3-dioxo-2H-isoindol-2-yl)benzeneacetic acid

Product 1

HCID 67517443HCID 67517443, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of [3-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)phenyl]acetic acid (0.75 g, 2.7 mmol) in DCM (25 mL) was added oxalyl chloride (0.28 mL, 3.2 mmol) and a drop of DMF. The mixture was allowed to stir at RT until all solids disappeared. At that point, the solution was cooled to to 0° C. with an ice bath, and aluminum chloride (1.1 g, 8.0 mmol) was added into the reaction slowly. After stirring the mixture for another 10 minutes, ethylene was bubbled through the reaction via a long needle. TLC showed complete reaction within 30 minutes. The reaction was poured into ice water, neutralized with sodium carbonate, extracted with DCM, dried, concentrated, and purified by MPLC (Hexane/EtOAc). LC-MS (IE, m/z): 292 [M+1]+.

Workup

  1. temperatureAt that point, the solution was cooled to to 0° C. with an ice bath
  2. stirringAfter stirring the mixture for another 10 minutes
  3. customethylene was bubbled through the reaction via a long needle
  4. customreaction within 30 minutes
  5. extractionextracted with DCM
  6. customdried
  7. concentrationconcentrated
  8. custompurified by MPLC (Hexane/EtOAc)

Sources & evidence

ORD record
ord-d9ca84ab0442408ebd5d18e79742e674
Source dataset
uspto-grants-2015_07
Patent number
US09073882B2

Reaction notes

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