Iodine → HCID 22723251, compound

HRID 2297708Notes

Reaction equation

HRID 2297708 reaction equation
II.[CH:3]1([CH2:9][CH2:10][N:11]2[CH2:15][CH2:14][S:13]C2)[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4]1.[OH-].[Na+]>CO>[CH:3]1([CH2:9][CH2:10][NH:11][CH2:15][CH2:14][S:13][S:13][CH2:14][CH2:15][NH:11][CH2:10][CH2:9][CH:3]2[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8]2)[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8]1

Participants

5

Reactant 3

HCID 807IodineHCID 14798Sodium HydroxideHCID 22723046HCID 22723046, compound

Product 1

HCID 22723251HCID 22723251, compoundYield 102.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

A solution of iodine (378 mg) in methanol (5 ml) is added dropwise to a solution of N-(2-cyclohexylethyl)thiazolidine (594 mg) in methanol (10 ml) at room temperature with stirring. After the dropping, the mixture is stirred at room temperature for 30 minutes. A 4 N aqueous sodium hydroxide solution (10 ml) is added to the reaction mixture, and the mixture is concentrated under reduced pressure. Chloroform is added to the concentrate, and the whole is extracted. The organic layer is washed with saturated brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure to give 571 mg (51%) of the titled compound (Reference compound No. 19-1).

Workup

  1. stirringAfter the dropping, the mixture is stirred at room temperature for 30 minutes
  2. concentrationthe mixture is concentrated under reduced pressure
  3. additionChloroform is added to the concentrate
  4. extractionthe whole is extracted
  5. washThe organic layer is washed with saturated brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-2800717bf4b5412cb8c2274462dd3ac3
Source dataset
uspto-grants-2002_12
Patent number
US06492370B1

Reaction notes

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