Sodium Iodide → HCID 58046761, compound

HRID 1750992Notes

Reaction equation

HRID 1750992 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[O: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[O:7][C:6]1=[O:14]

Participants

4

Reactant 2

HCID 5238Sodium IodideHCID 100360722(3H)-Benzoxazolone, 3-(3-chloropropyl)-

Product 1

HCID 58046761HCID 58046761, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of 3-(3-chloropropyl)benzo[d]oxazol-2(3H)-one (3.04 g, 14.36 mmol) in acetone (60 mL), was added sodium iodide (4.3 g, 28.73 mmol). After refluxing for 60 hours, the reaction mixture was filtered. The filtrate was washed with water and dried to obtain the title compound (3.6 g, 83%); 1H NMR (DMSO-d6): δ 2.19-2.24 (m, 2H), 3.28 (t, 2H, J=6.8 Hz), 3.87 (t, 2H, J=6.8 Hz), 7.11 (t, 1H, J=8 Hz), 7.22 (t, 1H, J=8 Hz), 7.32 (t, 2H, J=8.4 Hz). MS for C10H10INO2 m/z 304.33 (M+H)+.

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-f4c7ce992027415da92daf3a17cc2973
Source dataset
uspto-grants-2015_10
Patent number
US09156840B2

Reaction notes

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