Iodine → HCID 10476981, compound

HRID 865362Notes

Reaction equation

HRID 865362 reaction equation
[CH2:1]([N:4]([C:19]([O:21][CH2:22][C:23]1C=CC=CC=1)=[O:20])[C:5]1[CH:10]=[C:9]([F:11])[C:8]([C:12]2[CH:13]=[N:14][CH:15]=[CH:16][CH:17]=2)=[C:7]([F:18])[CH:6]=1)C=C.N1C=CC=CC=1.[I:35]I>C(Cl)(Cl)Cl>[I:35][CH2:23][CH:22]1[O:21][C:19](=[O:20])[N:4]([C:5]2[CH:6]=[C:7]([F:18])[C:8]([C:12]3[CH:13]=[N:14][CH:15]=[CH:16][CH:17]=3)=[C:9]([F:11])[CH:10]=2)[CH2:1]1

Participants

5

Reactant 3

HCID 807IodineHCID 1049PyridineHCID 9977053HCID 9977053, compound

Product 1

HCID 10476981HCID 10476981, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

N-Allyl-N-carbobenzyloxy-4-(3-pyridyl)-3,5-difluoroaniline (PREPARATION 4, 496 mg 1.31 mmol) in chloroform (25 ml), pyridine (1.58 ml, 19.6 mmol, 15 eq) and iodine (4.97 g, 19.6 mmol, 15 eq) are combined. The resulting mixture is placed under an atmosphere of nitrogen and heated to 50° with stirring. After 1.5 hr, the reaction is decanted into chloroform (70 ml). The remaining sludge is rinsed with chloroform (3×15 ml). The combined organics are washed with sodium thiosulfate (20%), then brine, dried (sodium sulfate), filtered and concentrated under reduced pressure to give a solid. This material is purified by silica gel chromatography (100 g) eluting with methanol/chloroform (0.5/99.5 - 11, 1/99, 11). The appropriate fractions are pooled and concentrated to give the title compound, mp 133°-134°; FTIR (mull) cm-1 3130, 1758, 1650, 1414, 1241, 1017 and 846; NMR (CDCl3) 8.72, 8.62, 7.79, 7.43-7.38, 7.32, 4.84-4.72, 4.19, 3.80, 3.51 and 3.39 δ.

Workup

  1. temperatureheated to 50°
  2. customthe reaction is decanted into chloroform (70 ml)
  3. washThe remaining sludge is rinsed with chloroform (3×15 ml)
  4. washThe combined organics are washed with sodium thiosulfate (20%)
  5. dry with materialbrine, dried (sodium sulfate)
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customto give a solid
  9. customThis material is purified by silica gel chromatography (100 g)
  10. washeluting with methanol/chloroform (0.5/99.5 - 11, 1/99, 11)
  11. concentrationconcentrated

Sources & evidence

ORD record
ord-8b825c4570084cebb5de7a39bb81d5a1
Source dataset
uspto-grants-1996_10
Patent number
US05565571

Reaction notes

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