Sodium Iodide → HCID 11573971, compound

HRID 1261187Notes

Reaction equation

HRID 1261187 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([N:9]2[CH:13]([CH3:14])[CH2:12][C:11]([OH:15])=[N:10]2)[CH:5]=[CH:6][C:7]=1[Cl:8].Cl.Cl[CH2:18][CH2:19][N:20]1[CH2:25][CH2:24][O:23][CH2:22][CH2:21]1.C([O-])([O-])=O.[K+].[K+].[Na+].[I-]>CN(C)C=O.O>[Cl:1][C:2]1[CH:3]=[C:4]([N:9]2[C:13]([CH3:14])=[CH:12][C:11]([O:15][CH2:18][CH2:19][N:20]3[CH2:25][CH2:24][O:23][CH2:22][CH2:21]3)=[N:10]2)[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

7

Reactant 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 77210Morpholine, 4-(2-chloroethyl)-, hydrochloride (1:1)HCID 178429551HCID 178429551, compound

Product 1

HCID 11573971HCID 11573971, compoundYield 69.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of (VI) (300 mg, 1.23 mmol), N-(2-chloroethyl)morpholine hydrochloride (230 mg, 123 mmol), K2CO3 (341 mg, 2.47 mmol), and NaI (185 mg, 1.23 mmol) in dry dimethyl formamide (5 ml) was stirred overnight at 70° C. The mixture was poured into water (20 ml), extracted four times with Et2O, and the organic extracts were washed with saturated NaCl solution, dried (Na2SO4), and concentrated in vacuo. The residue was purified via MPLC (light petroleum/AcOEt 4:1) to yield (VII) (303 mg, 69%) as a colorless oil. TLC CHCl3/MeOH 9:1.

Workup

  1. extractionextracted four times with Et2O
  2. washthe organic extracts were washed with saturated NaCl solution
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified via MPLC (light petroleum/AcOEt 4:1)

Sources & evidence

ORD record
ord-f6f17fc3601f407f9a43fa374c1a0610
Source dataset
uspto-grants-2013_06
Patent number
US08470867B2

Reaction notes

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