Sodium Iodide → HCID 9879445, compound

HRID 1293111Notes

Reaction equation

HRID 1293111 reaction equation
Cl[CH2:2][CH2:3][CH2:4][C:5]1[S:9][C:8]2[CH:10]=[CH:11][CH:12]=[CH:13][C:7]=2[CH:6]=1.[I-:14].[Na+].S([O-])([O-])(=O)=S.[Na+].[Na+]>CC(C)=O>[I:14][CH2:2][CH2:3][CH2:4][C:5]1[S:9][C:8]2[CH:10]=[CH:11][CH:12]=[CH:13][C:7]=2[CH:6]=1

Participants

5

Reactant 3

HCID 5238Sodium IodideHCID 24477Sodium ThiosulfateHCID 152125492-(3-Chloropropyl)benzo[b]thiophene

Product 1

HCID 9879445HCID 9879445, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 2-(3-Chloro-propyl)-benzo[b]thiophene (902 mg, 4.28 mmol) and sodium iodide (1.29 g, 8.6 mmol) was heated to 50° C. in acetone (5 ml) for 72 h, then cooled to room temperature. Aqueous sodium thiosulphate (1 M, 10 ml) was added and the product was extracted with diethyl ether (2×20 ml). The organic layer was dried (K2CO3), filtered and concentrated in vacuo to give a white solid that was filtered through Celite and eluted with heptanes. The filtrate was concentrated in vacuo to give a white solid. Yield 1.038 g (80%). 1H NMR (CDCl3): δ 2.24 (tt, 2H), 3.04 (dt, 2H), 3.27 (t, 2H), 7.07 (q, 1H), 7.28 (m, 2H), 7.68 (m, 1H), 7.77 (m, 1H).

Workup

  1. extractionthe product was extracted with diethyl ether (2×20 ml)
  2. dry with materialThe organic layer was dried (K2CO3)
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customto give a white solid
  6. filtrationthat was filtered through Celite
  7. washeluted with heptanes
  8. concentrationThe filtrate was concentrated in vacuo
  9. customto give a white solid

Sources & evidence

ORD record
ord-e447b7b6b9904e42bbbc232a49ac6762
Source dataset
uspto-grants-2007_07
Patent number
US07238713B2

Reaction notes

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