Sodium Iodide → HCID 58046761, compound

HRID 2362917Notes

Reaction equation

HRID 2362917 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 refuxing 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. filtrationthe reaction mixture was filtered
  2. washThe filtrate was washed with water
  3. customdried

Sources & evidence

ORD record
ord-e50c4705babf4726ab89e2c2cccfdd57
Source dataset
uspto-grants-2014_04
Patent number
US08691836B2

Reaction notes

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