Oxalyl chloride → HCID 66881434, compound

HRID 1893566Notes

Reaction equation

HRID 1893566 reaction equation
[CH2:1]([O:3][C:4](=[O:25])[CH2:5][N:6]([CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21])[C:7]1[CH:12]=[C:11]([CH2:13][CH2:14][C:15]([OH:17])=O)[CH:10]=[CH:9][C:8]=1[CH3:18])[CH3:2].C(Cl)(=O)C(Cl)=O.[Cl-].[Al+3].[Cl-].[Cl-]>CN(C)C=O.ClCCl>[CH2:1]([O:3][C:4](=[O:25])[CH2:5][N:6]([CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21])[C:7]1[CH:12]=[C:11]2[C:10](=[CH:9][C:8]=1[CH3:18])[C:15](=[O:17])[CH2:14][CH2:13]2)[CH3:2]

Participants

6

Reactant 3

HCID 65578Oxalyl chlorideHCID 6451240Aluminum(III) ChlorideHCID 66882050HCID 66882050, compound

Product 1

HCID 66881434HCID 66881434, compoundYield 57.1%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent2×

Conditions

Temperature
40 °C

Procedure

To dichloromethane (68 ml) were added the compound (4.79 g, 13.6 mmol) obtained in step C, N,N-dimethylformamide (5 drops) and oxalyl chloride (2.59 g, 20.4 mmol), and the mixture was stirred at 40° C. for 3 hr. The reaction mixture was concentrated under reduced pressure, and the obtained oil was diluted with dichloroethane (68 ml) and cooled in an ice water bath. To this solution was added aluminum chloride (2.54 g, 19.0 mmol) by small portions, and the mixture was stirred at 90° C. for 4 hr. The reaction mixture was diluted with dichloromethane, washed with water and saturated brine, and dried over sodium sulfate. The insoluble material was filtered off, and the solution was concentrated under reduced pressure. The obtained oil was purified by silica gel column chromatography (ethyl acetate-hexane) to give the title compound (2.59 g, yield 57%) as a colorless oil.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. additionthe obtained oil was diluted with dichloroethane (68 ml)
  3. temperaturecooled in an ice water bath
  4. stirringthe mixture was stirred at 90° C. for 4 hr
  5. washwashed with water and saturated brine
  6. dry with materialdried over sodium sulfate
  7. filtrationThe insoluble material was filtered off
  8. concentrationthe solution was concentrated under reduced pressure
  9. customThe obtained oil was purified by silica gel column chromatography (ethyl acetate-hexane)

Sources & evidence

ORD record
ord-e0b583265cfb410799045c63ed8b8cbb
Source dataset
uspto-grants-2013_08
Patent number
US08513235B2

Reaction notes

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