Sodium Iodide → 3-(3-Iodopropyl)-3H-benzothiazol-2-one

HRID 2362920Notes

Reaction equation

HRID 2362920 reaction equation
Cl[CH2:2][CH2:3][CH2:4][N:5]1[C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=2[S:7][C:6]1=[O:14].[I-:15].[Na+]>CC(C)=O>[I:15][CH2:2][CH2:3][CH2:4][N:5]1[C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=2[S:7][C:6]1=[O:14]

Participants

4

Reactant 2

HCID 5238Sodium IodideHCID 219898853-(3-chloropropyl)benzo[d]thiazol-2(3H)-one

Product 1

HCID 219900133-(3-Iodopropyl)-3H-benzothiazol-2-oneYield 96%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of 3-(3-chloropropyl)benzo[d]thiazol-2(3H)-one (2.86 g, 12.56 mmol) in acetone (50 mL), was added sodium iodide (3.77 g, 25.12 mmol). After refuxing for 60 hours, the reaction mixture was filtered. The filtrate was washed with water and dried to obtain the title compound (3.85 g, 83%); 1H NMR (DMSO-d6): δ 2.13-2.16 (m, 2H), 3.28 (t, 2H, J=6.8 Hz), 4.05 (t, 2H, J=6.8 Hz), 7.18-7.22 (m, 1H), 7.38-7.39 (m, 2H), 7.66 (dt, 1H, J=7.6 and 0.8 Hz).

Workup

  1. filtrationthe reaction mixture was filtered
  2. washThe filtrate was washed with water
  3. customdried

Sources & evidence

ORD record
ord-7e846af07b9c431a90eb3985c6993fd3
Source dataset
uspto-grants-2014_04
Patent number
US08691836B2

Reaction notes

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