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

HRID 1750995Notes

Reaction equation

HRID 1750995 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 refluxing 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. temperatureAfter refluxing for 60 hours
  2. filtrationthe reaction mixture was filtered
  3. washThe filtrate was washed with water
  4. customdried

Sources & evidence

ORD record
ord-ae9c6ff204854ab0bab2328a739719b6
Source dataset
uspto-grants-2015_10
Patent number
US09156840B2

Reaction notes

Loading…