Trifluoromethanesulfonic acid → HCID 22594391, compound

HRID 457241Notes

Reaction equation

HRID 457241 reaction equation
[I:1]N1C(=O)CCC1=O.[F:9][C:10]([F:23])([F:22])[C:11]1[CH:19]=[C:18]2[C:14]([C:15](=[O:21])[C:16](=[O:20])[NH:17]2)=[CH:13][CH:12]=1.OS(C(F)(F)F)(=O)=O>>[I:1][C:12]1[CH:13]=[C:14]2[C:18](=[CH:19][C:11]=1[C:10]([F:9])([F:22])[F:23])[NH:17][C:16](=[O:20])[C:15]2=[O:21]

Participants

4

Reactant 3

HCID 62406Trifluoromethanesulfonic acidHCID 120273N-IodosuccinimideHCID 109876496-Trifluoromethylisatin

Product 1

HCID 22594391HCID 22594391, compoundYield 63.8%

Procedure

N-Iodosuccinimide (25.0 g, 119.5 mmol) was added to a stirred mixture of 6-trifluoromethylisatin (10.3 g, 47.8 mmol) and triflic acid (75 g) at 0° C. under nitrogen. The ice bath was removed and stirring at room temperature was continued for 7 h. The mixture was poured into ice-water and was extracted with EtOAc. The combined organic extracts were evaporated under reduced pressure and the residue was triturated with CHCl3 to produce a yellow-orange solid. Filtration of the crude solid and purification by recrystallization from CHCl3 gave 5-iodo-6-trifluoromethylisatin xxxiii (10.4 g) as an orange solid. 1H NMR (DMSO-d6) δ 7.17(s, 1 H), 8.08(s, 1 H), 11.27(s, 1 H); ms 340.0 (M−H).

Workup

  1. customThe ice bath was removed
  2. additionThe mixture was poured into ice-water
  3. extractionwas extracted with EtOAc
  4. customThe combined organic extracts were evaporated under reduced pressure
  5. customthe residue was triturated with CHCl3
  6. customto produce a yellow-orange solid
  7. filtrationFiltration of the crude
  8. customsolid and purification
  9. customby recrystallization from CHCl3

Sources & evidence

ORD record
ord-626888da8216479f986722914f6ea995
Source dataset
uspto-grants-2007_03
Patent number
US07186841B2

Reaction notes

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