Oxalyl chloride → HCID 10586213, compound

HRID 1666882Notes

Reaction equation

HRID 1666882 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[CH:5]2.[C:11](Cl)(=[O:15])[C:12]([Cl:14])=[O:13]>C(OCCCC)CCC>[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[C:5]2[C:11](=[O:15])[C:12]([Cl:14])=[O:13]

Participants

4

Reactant 2

HCID 65578Oxalyl chlorideHCID 871105-Chloroindole

Product 1

HCID 10586213HCID 10586213, compound

Reagents, catalysts & solvents 1

HCID 8909Butyl etherSolvent

Procedure

Combine 5-chloroindole (20 g, 0.13 mole) and dibutyl ether (230 mL) and cool to 5° C. and slowly add the oxalyl chloride (20.08 g, 0.16 mole) over 15 min while maintaining the temperature between 5° C. and 10° C. Warm to room temperature and stir for 1 hour to give a solid. Cool to 5° C. and stir for 15 minutes, collect the solid by filtration, wash with dibutyl ether, and dry under vacuum to give the title compound.

Workup

  1. temperaturewhile maintaining the temperature between 5° C. and 10° C
  2. customto give a solid
  3. temperatureCool to 5° C.
  4. stirringstir for 15 minutes
  5. customcollect the solid
  6. filtrationby filtration
  7. washwash with dibutyl ether
  8. customdry under vacuum

Sources & evidence

ORD record
ord-fadeaf0eed8646899e61d417f4cdaa3b
Source dataset
uspto-grants-2011_10
Patent number
US08044090B2

Reaction notes

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