Iodine → HCID 22908973, compound

HRID 1378988Notes

Reaction equation

HRID 1378988 reaction equation
[CH3:1][N:2]1[C:10]2[C:9](=[O:11])[N:8]([CH2:12][CH2:13][CH3:14])[C:7](=[O:15])[N:6]([CH2:16][CH2:17][CH3:18])[C:5]=2[N:4]=[C:3]1/[CH:19]=[CH:20]\[C:21]1[CH:26]=[CH:25][C:24]([C:27]([OH:29])=[O:28])=[CH:23][CH:22]=1.II.S([O-])([O-])(=O)=S.[Na+].[Na+].C(Cl)(Cl)Cl>C1(C)C=CC=CC=1>[CH3:1][N:2]1[C:10]2[C:9](=[O:11])[N:8]([CH2:12][CH2:13][CH3:14])[C:7](=[O:15])[N:6]([CH2:16][CH2:17][CH3:18])[C:5]=2[N:4]=[C:3]1/[CH:19]=[CH:20]/[C:21]1[CH:22]=[CH:23][C:24]([C:27]([OH:29])=[O:28])=[CH:25][CH:26]=1

Participants

6

Reactant 4

HCID 807IodineHCID 6212ChloroformHCID 24477Sodium ThiosulfateHCID 70046769HCID 70046769, compound

Product 1

HCID 22908973HCID 22908973, compoundYield 59.3%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 1.25 g (3.15 mmol) of Compound 18 obtained in Example 17 and 40 mg (0.32 mmol) of iodine in 125 ml of toluene was heated under reflux for 6.5 hours. After cooling, a 0.1M aqueous solution of sodium thiosulfate and chloroform were added thereto, followed by stirring. The precipitated crystals were collected by filtration, and recrystallized from ethanol to give 740 mg (yield 59%) of Compound 19 as ocher needles.

Workup

  1. temperatureunder reflux for 6.5 hours
  2. temperatureAfter cooling
  3. filtrationThe precipitated crystals were collected by filtration
  4. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-0868fb9c52234950ab89c0cfbf3afb4a
Source dataset
uspto-grants-1997_09
Patent number
US05670498

Reaction notes

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