Iodine → HCID 18625666, compound

HRID 1859487Notes

Reaction equation

HRID 1859487 reaction equation
[CH3:1][N:2]1[C:7]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10]C=2)=[C:6]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH:5]([CH2:19][CH3:20])[C:4]([C:21]([S:23][CH2:24][CH3:25])=[O:22])=[C:3]1[CH2:26][CH3:27].II>[N+](C)([O-])=O>[CH3:1][N:2]1[C:7]([CH:8]2[CH2:10][CH2:11][CH2:12][CH2:13]2)=[C:6]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH:5]([CH2:19][CH3:20])[C:4]([C:21]([S:23][CH2:24][CH3:25])=[O:22])=[C:3]1[CH2:26][CH3:27]

Participants

4

Reactant 2

HCID 807Iodine2×HCID 18625670HCID 18625670, compound2×

Product 1

HCID 18625666HCID 18625666, compoundYield 30%

Reagents, catalysts & solvents 1

HCID 6375NitromethaneSolvent

Procedure

Chemical Transformation of 24 to 11 through Oxidation with Iodine (Scheme 1): A solution of 24 (5 mg, 0.013 mmol) in 0.5 mL of dry nitromethane was treated with iodine (10 mg, 0.040 mmol) at room temperature with stirring for 1 day (monitor by TLC). At completion the reaction mixture was applied to TLC separation (ethyl acetate:petroleum ether=1:4 v/v for the first development then 1:1 for a second development), and 2 mg of a yellow solid was obtained (yield: 30%), with 1H-NMR and MS data consistent with those of compound 11.

Workup

  1. customAt completion the reaction mixture was applied to TLC separation (ethyl acetate

Sources & evidence

ORD record
ord-cb0d15e6968646688e1b7780c55ccdfe
Source dataset
uspto-grants-2003_03
Patent number
US06528516B1

Reaction notes

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