Sodium Iodide → HCID 19737957, compound

HRID 2255512Notes

Reaction equation

HRID 2255512 reaction equation
[CH3:1][CH:2]1[C:6]2[CH:7]=[CH:8][S:9][C:5]=2[S:4](=[O:11])(=[O:10])[NH:3]1.[H-].[Na+].Cl.Cl[CH2:16][CH2:17][N:18]1[CH2:23][CH2:22][O:21][CH2:20][CH2:19]1.[Na+].[I-]>CN(C=O)C.O>[CH3:1][CH:2]1[C:6]2[CH:7]=[CH:8][S:9][C:5]=2[S:4](=[O:11])(=[O:10])[N:3]1[CH2:16][CH2:17][N:18]1[CH2:23][CH2:22][O:21][CH2:20][CH2:19]1

Participants

7

Reactant 4

HCID 5238Sodium IodideHCID 24758Sodium hydrideHCID 77210Morpholine, 4-(2-chloroethyl)-, hydrochloride (1:1)HCID 19738010HCID 19738010, compound

Product 1

HCID 19737957HCID 19737957, compoundYield 98.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

The product from Step B (1.06 g, 5.62 mmol) was added to a suspension of NaH (0.97 g, 22.5 mmol) in DMF (19 mL) followed by chloroethylmorpholine hydrochloride (2.11 g, 11.21 mmol), and the mixture was warmed to 80° C. at which point NaI (1.1 g) was added and the mixture stirred for 20 min. The reaction mixture was diluted with water (80 mL) and extracted with methylene chloride (3×25 mL). The combined extracts were evaporated to a residue which was dissolved in ethyl acetate (80 mL) and the solution was extracted with 2N HCl (3×20 mL); this aqueous solution was adjusted to pH 7.5 with 2N NaOH and extracted with ethyl acetate (3×15 mL). The combined extracts were dried (MgSO4) and evaporated to a residue which was purified by column chromatography [silica, CH2Cl2 /CH3OH(3:1)] to give 1.68 g (98%) of the desired product as an oil.

Workup

  1. additionwas added
  2. extractionextracted with methylene chloride (3×25 mL)
  3. customThe combined extracts were evaporated to a residue which
  4. dissolutionwas dissolved in ethyl acetate (80 mL)
  5. extractionthe solution was extracted with 2N HCl (3×20 mL)
  6. extractionextracted with ethyl acetate (3×15 mL)
  7. dry with materialThe combined extracts were dried (MgSO4)
  8. customevaporated to a residue which
  9. customwas purified by column chromatography [silica, CH2Cl2 /CH3OH(3:1)]

Sources & evidence

ORD record
ord-b959e85b9a2a42e8a1882ec13a61d681
Source dataset
uspto-grants-1993_08
Patent number
US05240923

Reaction notes

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