Oxalyl chloride → HCID 15023219, compound

HRID 1651314Notes

Reaction equation

HRID 1651314 reaction equation
[C:1]([C:3](=[C:7]([C:15]1[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=1)[C:8]1[CH:13]=[CH:12][C:11]([F:14])=[CH:10][CH:9]=1)[C:4](O)=[O:5])#[N:2].C(Cl)(=O)C([Cl:25])=O>C(Cl)Cl>[C:1]([C:3](=[C:7]([C:15]1[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=1)[C:8]1[CH:13]=[CH:12][C:11]([F:14])=[CH:10][CH:9]=1)[C:4]([Cl:25])=[O:5])#[N:2]

Participants

4

Reactant 2

HCID 65578Oxalyl chlorideHCID 14890664HCID 14890664, compound

Product 1

HCID 15023219HCID 15023219, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of 2-cyano-3,3-bis(4-fluorophenyl)-2-propenoic acid (4 g, 14 mmol) in 10 mL of dry methylene chloride at room temperature was added oxalyl chloride (6 mL, 69 mmol) in one single portion. The reaction was stirred and warmed slowly to reflux for 45 minutes. The pale homogeneous solution was evaporated under reduced pressure to remove volatile solvent, then excess oxalyl chloride was removed under vacuum (20 mm Hg) at ambient temperature for 2 hours and under high vacuum (0.1 mm Hg) for 16 hours to give the title compound.

Workup

  1. temperaturewarmed slowly
  2. temperatureto reflux for 45 minutes
  3. customThe pale homogeneous solution was evaporated under reduced pressure
  4. customto remove volatile solvent
  5. customexcess oxalyl chloride was removed under vacuum (20 mm Hg) at ambient temperature for 2 hours and under high vacuum (0.1 mm Hg) for 16 hours

Sources & evidence

ORD record
ord-97f65c2ac3bd4b69a32529b5d7ed6d37
Source dataset
uspto-grants-1990_05
Patent number
US04927944

Reaction notes

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