Oxalyl chloride → HCID 86741186, compound

HRID 979819Notes

Reaction equation

HRID 979819 reaction equation
[CH2:1]([O:3][C:4]([N:6]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][C:13]=2[CH2:15][CH2:16][CH2:17][C:18]([O:20]CC)=O)[CH2:8][CH2:7]1)=[O:5])[CH3:2].C(Cl)(=O)C(Cl)=O>C1C=CC=CC=1>[O:20]=[C:18]1[C:12]2=[CH:11][CH:10]=[C:9]3[C:14]([N:6]([C:4]([O:3][CH2:1][CH3:2])=[O:5])[CH2:7][CH2:8]3)=[C:13]2[CH2:15][CH2:16][CH2:17]1

Participants

4

Reactant 2

HCID 65578Oxalyl chlorideHCID 86741187HCID 86741187, compound

Product 1

HCID 86741186HCID 86741186, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Conditions

Temperature
50 °C

Procedure

The product from Example 115 (2.7 g) was dissolved in benzene (25 ml) and oxalyl chloride (2.6 ml) was added. The resulting solution was heated at 50° C. for 30 minutes, then the solvent was evaporated to dryness. The residue was dissolved in methylene chloride (30 ml), cooled to 0° C., and aluminum chloride (4 g) was added. The reaction mixture was stirred at 0° C. for 1 hour then quenched with ice and hydrochloric acid then extracted with methylene chloride. The organic layer was separated, washed with brine, dried and evaporated in vacuo affording the desired product in 50% yield.

Workup

  1. customthe solvent was evaporated to dryness
  2. dissolutionThe residue was dissolved in methylene chloride (30 ml)
  3. temperaturecooled to 0° C.
  4. additionaluminum chloride (4 g) was added
  5. customthen quenched with ice and hydrochloric acid
  6. extractionthen extracted with methylene chloride
  7. customThe organic layer was separated
  8. washwashed with brine
  9. customdried
  10. customevaporated in vacuo

Sources & evidence

ORD record
ord-588185070d694d29b55baf03ebe01997
Source dataset
uspto-grants-1987_01
Patent number
US04634705

Reaction notes

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