Iodine chloride → HCID 22724558, compound

HRID 1841519Notes

Reaction equation

HRID 1841519 reaction equation
[N+:1]([C:4]1[CH:16]=[CH:15][C:7]([CH:8]=[C:9]2[CH2:14][CH2:13][O:12][CH2:11][CH2:10]2)=[CH:6][CH:5]=1)([O-])=O.C([O-])(=O)C.[Na+].[I:22]Cl>C(Cl)(Cl)Cl.CO.O=[Pt]=O>[I:22][C:5]1[CH:6]=[C:7]([CH2:8][CH:9]2[CH2:14][CH2:13][O:12][CH2:11][CH2:10]2)[CH:15]=[CH:16][C:4]=1[NH2:1]

Participants

7

Reactant 3

HCID 24640Iodine chlorideHCID 517045Sodium AcetateHCID 22724551HCID 22724551, compound

Product 1

HCID 22724558HCID 22724558, compoundYield 34%

Reagents, catalysts & solvents 3

HCID 345198Adams' catalystCatalystHCID 887MethanolSolvent2×HCID 6212ChloroformSolvent

Procedure

A mixture of 4-(4-nitrobenzylidene)tetrahydro-2H-pyran (2.0 g) and PtO2 (0.2 g) is hydrogenated at 40 p.s.i. H2 for 3.5 h. The mixture is filtered through celite and the filtrate is condensed. The crude residue is dissolved in a mixture of 40 mL CHCl3 and 4 mL MeOH. To this is added sodium acetate (2.24 g), followed by the dropwise addition of a solution of ICl (0.69 mL) in MeOH (10 mL). The reaction is stirred at room temperature for 1 h then quenched by pouring into an iced saturated solution of aqueous sodium bisulfite (200 mL). The mixture is stirred for 30 minutes then concentrated to remove organic solvents. The aqueous solution is extracted with CH2Cl2 (3×). The combined organic layers are washed with brine, dried and condensed. The crude product is chromatographed (Biotage flash 40M, eluant CH2Cl2) to yield 1.0 g (34%) of 2-iodo-4-(tetrahydro-2H-pyran-4-ylmethyl)aniline as an oil.

Workup

  1. filtrationThe mixture is filtered through celite
  2. customcondensed
  3. customthen quenched
  4. additionby pouring into an iced saturated solution of aqueous sodium bisulfite (200 mL)
  5. stirringThe mixture is stirred for 30 minutes
  6. concentrationthen concentrated
  7. customto remove organic solvents
  8. extractionThe aqueous solution is extracted with CH2Cl2 (3×)
  9. washThe combined organic layers are washed with brine
  10. customdried
  11. customcondensed
  12. customThe crude product is chromatographed (Biotage flash 40M, eluant CH2Cl2)

Sources & evidence

ORD record
ord-65ef5c1aa19f43b0af3c140232266b07
Source dataset
uspto-grants-2004_01
Patent number
US06683181B2

Reaction notes

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