Sodium Iodide → HCID 66653897, compound

HRID 571787Notes

Reaction equation

HRID 571787 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][S:11][CH:10]([C:14]2[CH:19]=[CH:18][C:17](Br)=[CH:16][CH:15]=2)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].CNCCNC.[Na+].[I-:28]>O1CCOCC1.[Cu]I>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][S:11][CH:10]([C:14]2[CH:19]=[CH:18][C:17]([I:28])=[CH:16][CH:15]=2)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 3

HCID 5238Sodium IodideHCID 8070N,N'-DimethylethylenediamineHCID 66653556HCID 66653556, compound

Product 1

HCID 66653897HCID 66653897, compoundYield 41.3%

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 degassed solution of 2-(4-bromo-phenyl)-thiomorpholine-4-carboxylic acid tert-butyl ester (0.75 g; 2.09 mmol) and N,N′-dimethylethylenediamine (0.11 mL; 1.05 mmol) in 1,4-dioxane (10 mL) was added CuI (39.9 mg; 0.21 mmol) and NaI (0.78 g; 5.23 mmol). The resulting mixture was heated in a closed vessel, at 130° C., for 3 days. After cooling to room temperature the mixture was concentrated in vacuo, and the residue was purified by column chromatography (SiO2, CH2Cl2/hexanes 1:1) to afford 2-(4-iodo-phenyl)-thiomorpholine-4-carboxylic acid tert-butyl ester (0.35 g).

Workup

  1. temperatureAfter cooling to room temperature the mixture
  2. concentrationwas concentrated in vacuo
  3. customthe residue was purified by column chromatography (SiO2, CH2Cl2/hexanes 1:1)

Sources & evidence

ORD record
ord-963990763ead4a788cf9bc689b4563de
Source dataset
uspto-grants-2015_05
Patent number
US09029371B2

Reaction notes

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