Diglyme → HCID 20026156, compound

HRID 1722920Notes

Reaction equation

HRID 1722920 reaction equation
[Cl:1][C:2]1[C:7](OC=C)=[CH:6][C:5]([N:11]2[C:15](=[O:16])[C:14]3[CH2:17][CH2:18][CH2:19][CH2:20][C:13]=3[C:12]2=[O:21])=[C:4]([F:22])[CH:3]=1.Cl[C:24]([F:29])([F:28])[C:25]([O-])=[O:26].[Na+].[CH3:31]OCCOCCOC>>[Cl:1][C:2]1[C:7]([O:26][CH:25]2[CH2:31][C:24]2([F:29])[F:28])=[CH:6][C:5]([N:11]2[C:12](=[O:21])[C:13]3[CH2:20][CH2:19][CH2:18][CH2:17][C:14]=3[C:15]2=[O:16])=[C:4]([F:22])[CH:3]=1

Participants

4

Reactant 3

HCID 8150Diglyme2×HCID 2734985Sodium chlorodifluoroacetateHCID 20026153HCID 20026153, compound

Product 1

HCID 20026156HCID 20026156, compound

Procedure

1.2 g N-[4-Chloro-2-fluoro-5-vinyloxyphenyl)-3,4,5,6-tetrahydrophthalimide was dissolved in 5 ml diethylene glycol dimethyl ether, the mixture was heated to reflux and a solution of 2.8 g sodium chlorodifluoroacetate in 5 ml diethylene glycol dimethyl ether was added slowly. The mixture was heated under reflux for 5 hours, then separated from the sodium chloride, which formed, and the solvent removed. The residue was chromatographed on silica gel using a mixture of hexane/diethyl ether=1:1.

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux
  3. temperatureThe mixture was heated
  4. temperatureunder reflux for 5 hours
  5. customseparated from the sodium chloride, which
  6. customformed
  7. customthe solvent removed
  8. customThe residue was chromatographed on silica gel using
  9. additiona mixture of hexane/diethyl ether=1:1

Sources & evidence

ORD record
ord-13d260d505844a3d98712301ad36176e
Source dataset
uspto-grants-1989_08
Patent number
US04859230

Reaction notes

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