Bis(trifluoroacetoxy)iodobenzene → HCID 57831017, compound

HRID 240318Notes

Reaction equation

HRID 240318 reaction equation
[C:1]([C:3]1[N:4]=[C:5]2[C:18](=NO)[C:17]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=3[C:6]2=[N:7][C:8]=1[C:9]([NH2:11])=[O:10])#[N:2].FC(F)(F)C(OI(C1C=CC=CC=1)OC(=O)C(F)(F)F)=[O:24]>CC#N.O>[C:1]([C:3]1[N:4]=[C:5]2[C:18](=[O:24])[C:17]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=3[C:6]2=[N:7][C:8]=1[C:9]([NH2:11])=[O:10])#[N:2]

Participants

4

Reactant 2

HCID 102317Bis(trifluoroacetoxy)iodobenzeneHCID 178510554HCID 178510554, compound

Product 1

HCID 57831017HCID 57831017, compoundYield 58%

Reagents, catalysts & solvents 1

HCID 18373917Acetonitrile--water (1/1)Solvent

Procedure

A suspension of 33 (522 mg, 1.97 mmol) and [bis(trifluoroacetoxy)iodo]benzene (1.69 g, 3.9 mmol) in CH3CN/H2O (9:1, 20 ml) was stirred 24 h at room temperature. The solid was collected by filtration and washed with CH3CN. The residue was dissolved in DMSO (2 ml) and precipitated by addition of H2O. The obtained solid was filtered and dried under vacuum, affording 36 (286 mg, 58%) as light brown solid. 1H NMR (300 MHz, DMSO d6): δ 8.65 (bs, 1H), 8.31 (bs, 1H), 8.09 (dd, 1H), 7.93 (m, 2H), 7.77 (ddd, 1H). ESI+MS: calcd for C13H6N4O2: 250.22; found: 251.1 (MH+).

Workup

  1. filtrationThe solid was collected by filtration
  2. washwashed with CH3CN
  3. dissolutionThe residue was dissolved in DMSO (2 ml)
  4. customprecipitated by addition of H2O
  5. filtrationThe obtained solid was filtered
  6. customdried under vacuum

Sources & evidence

ORD record
ord-5e1a7a796765490dbb757b7ddc31d46d
Source dataset
uspto-grants-2014_02
Patent number
US08648076B2

Reaction notes

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