Iodine → HCID 22723251, compound

HRID 1581812Notes

Reaction equation

HRID 1581812 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-4fbe3b354ff74f5d8ca342f78737e5a1
Source dataset
uspto-grants-2004_05
Patent number
US06730784B2

Reaction notes

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