Sodium Iodide → HCID 66654135, compound

HRID 920578Notes

Reaction equation

HRID 920578 reaction equation
[C:1]([O:5][C:6](=[O:22])[CH2:7][CH2:8][N:9]1[CH2:14][CH2:13][S:12][CH:11]([C:15]2[CH:20]=[CH:19][C:18](Br)=[CH:17][CH:16]=2)[CH2:10]1)([CH3:4])([CH3:3])[CH3:2].CNCCNC.[Na+].[I-:30]>[Cu]I.O1CCOCC1>[C:1]([O:5][C:6](=[O:22])[CH2:7][CH2:8][N:9]1[CH2:14][CH2:13][S:12][CH:11]([C:15]2[CH:20]=[CH:19][C:18]([I:30])=[CH:17][CH:16]=2)[CH2:10]1)([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 3

HCID 5238Sodium IodideHCID 8070N,N'-DimethylethylenediamineHCID 66653735HCID 66653735, compound

Product 1

HCID 66654135HCID 66654135, compoundYield 77.7%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
130 °C

Procedure

To a solution of 3-[2-(4-bromo-phenyl)-thiomorpholin-4-yl]-propionic acid tert-butyl ester (22.15 g; 57.33 mmol) 1,4-dioxane (250 mL) was added N,N′-dimethylethylene-diamine (3.05 mL; 28.67 mmol). Through the resulting mixture was bubbled nitrogen gas for 1 hour, and subsequently CuI (1.09 g; 5.73 mmol), and NaI (21.48 g; 143.33 mmol) were added. The resulting mixture was heated at 130° C. in a closed vessel for 4 days. After cooling to RT the mixture was concentrated in vacuo, and the residue purified by column chromatography (SiO2, Et2O/hexanes 2:3) to afford 3-[2-(4-iodo-phenyl)-thiomorpholin-4-yl]-propionic acid tert-butyl ester (19.30 g)

Workup

  1. customThrough the resulting mixture was bubbled nitrogen gas for 1 hour
  2. temperatureAfter cooling to RT the mixture
  3. concentrationwas concentrated in vacuo
  4. customthe residue purified by column chromatography (SiO2, Et2O/hexanes 2:3)

Sources & evidence

ORD record
ord-f10f3ba6f84b4619959add08a956f2b4
Source dataset
uspto-grants-2016_03
Patent number
US09273017B2

Reaction notes

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