Oxalyl chloride → HCID 14626892, compound

HRID 1085085Notes

Reaction equation

HRID 1085085 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]([O:14][C:15]2[CH:20]=[CH:19][C:18]([NH:21][C:22]([NH:24][C:25](=[O:34])[C:26]3[C:31]([F:32])=[CH:30][CH:29]=[CH:28][C:27]=3[F:33])=[O:23])=[CH:17][N:16]=2)[C:10]([F:13])([F:12])[F:11])[CH:5]=[CH:6][C:7]=1[Cl:8].[C:35](Cl)(=[O:39])[C:36](Cl)=[O:37]>ClCCCl>[F:33][C:27]1[CH:28]=[CH:29][CH:30]=[C:31]([F:32])[C:26]=1[C:25]([N:24]1[C:36](=[O:37])[C:35](=[O:39])[N:21]([C:18]2[CH:19]=[CH:20][C:15]([O:14][CH:9]([C:4]3[CH:5]=[CH:6][C:7]([Cl:8])=[C:2]([Cl:1])[CH:3]=3)[C:10]([F:12])([F:11])[F:13])=[N:16][CH:17]=2)[C:22]1=[O:23])=[O:34]

Participants

4

Reactant 2

HCID 65578Oxalyl chloride2×HCID 14626891HCID 14626891, compound

Product 1

HCID 14626892HCID 14626892, compoundYield 73.1%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

To a stirred solution of N-[[[2-[1-(3,4-dichlorophenyl)-2,2,2-trifluoroethoxy]pyridin-5-yl]amino]carbonyl]2,6-difluorobenzamide (1.0 g, 0.002 mole) in 1,2-dichloroethane (10 ml) was added oxalyl chloride (0.24 g, 0.0020 mole). This mixture was heated at reflux for five days. Additional oxalyl chloride (0.24 g) was added, and refluxing was continued for one more day. The solvent was removed from the reaction mixture by distillation under reduced pressure, leaving an oil. This oil was purified by column chromatography on silica gel, elution with toluene: ethyl acetate (9:1), yielding 0.84 g of 1-[(2,6-difluorophenyl)carbonyl]-3-[2-[1-(3,4-dichlorphenyl)2,2,2-trifluoroethoxy]pyridin-5-yl]imidazolidinetrione as a solid (mp 160° C.). The nmr and ir spectra were consistent with the proposed structure.

Workup

  1. temperatureThis mixture was heated
  2. temperatureat reflux for five days
  3. temperaturerefluxing
  4. customThe solvent was removed from the reaction mixture by distillation under reduced pressure
  5. customleaving an oil
  6. customThis oil was purified by column chromatography on silica gel, elution with toluene: ethyl acetate (9:1)

Sources & evidence

ORD record
ord-1cafd6f9480f48ca8f3b34aac08928e7
Source dataset
uspto-grants-1991_04
Patent number
US05008277

Reaction notes

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