Trifluoroacetic anhydride → HCID 131719368, compound

HRID 1720191Notes

Reaction equation

HRID 1720191 reaction equation
[N:1]([C:4]1[CH:19]=[CH:18][C:7]([S:8]/[C:9](=[C:13](\O)/[C:14]([OH:16])=[O:15])/[C:10](O)=[O:11])=[CH:6][CH:5]=1)=[C:2]=[S:3].FC(F)(F)C(OC(=O)C(F)(F)F)=O>C(Cl)(Cl)Cl>[N:1]([C:4]1[CH:19]=[CH:18][C:7]([S:8][C:9]2[C:10]([O:15][C:14](=[O:16])[CH:13]=2)=[O:11])=[CH:6][CH:5]=1)=[C:2]=[S:3]

Participants

4

Reactant 2

HCID 9845Trifluoroacetic anhydrideHCID 131719367HCID 131719367, compound

Product 1

HCID 131719368HCID 131719368, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

The 2-[4'-(Isothio-cyanato)thiophenoxy]-3-hydroxymaleic acid (4.510 g, 15.07 mmol) was slurried in 140 mL of CHCl3 under nitrogen, treated with trifluoroacetic anhydride (5.30 mL, 7.88 g, 37.5 mmol), and heated to reflux. After 6.5 hours, the homogeneous reaction mixture was allowed to cool to room temperature, concentrated, taken up in hot CCl4 (80 mL), filtered hot, concentrated to one third volume, and diluted with 10 mL of hexane. Crystallization occurred upon standing at room temperature over 30 minutes. After storing at 0° C. an additional 2 hours, the light orange crystals of 2-[4'-(isothiocyanato)thiophenoxy] maleic anhydride (the titled compound) were collected by filtration, washed twice with 30 mL portions of hexane and dried overnight under vacuum (0.05 mm Hg).

Workup

  1. temperatureheated to reflux
  2. concentrationconcentrated
  3. filtrationfiltered hot
  4. concentrationconcentrated to one third volume
  5. additiondiluted with 10 mL of hexane
  6. customCrystallization
  7. waitupon standing at room temperature over 30 minutes
  8. waitAfter storing at 0° C. an additional 2 hours
  9. filtrationthe light orange crystals of 2-[4'-(isothiocyanato)thiophenoxy] maleic anhydride (the titled compound) were collected by filtration
  10. washwashed twice with 30 mL portions of hexane
  11. customdried overnight under vacuum (0.05 mm Hg)

Sources & evidence

ORD record
ord-9e82c6b0fcec47128828987858749f4e
Source dataset
uspto-grants-1996_04
Patent number
US05505931

Reaction notes

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