Sodium Iodide → HCID 69482774, compound

HRID 2364262Notes

Reaction equation

HRID 2364262 reaction equation
Cl[CH2:2][CH2:3][N:4]1[CH2:9][CH2:8][CH2:7][CH2:6][S:5]1(=[O:11])=[O:10].[I-:12].[Na+]>CC(C)=O>[I:12][CH2:2][CH2:3][N:4]1[CH2:9][CH2:8][CH2:7][CH2:6][S:5]1(=[O:11])=[O:10]

Participants

4

Reactant 2

HCID 5238Sodium IodideHCID 28917003HCID 28917003, compound

Product 1

HCID 69482774HCID 69482774, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 2-(2-chloroethyl)tetrahydro-2H-1,2-thiazine 1,1-dioxide (1.3 g, 6.6 mmol) in acetone (13 mL) was added sodium iodide (4.9 g, 33 mmol). The reaction mixture was heated at 80° C. overnight. The reaction mixture was cooled to room temperature and filtered. The filtrate was concentrated in vacuo. The solids were taken up in dichloromethane and filtered. The filtrate was concentrated and chromatographed (0 to 5%, methanol in dichloromethane) to provide 2-(2-iodoethyl)tetrahydro-2H-1,2-thiazine 1,1-dioxide as an orange solid. 1H NMR (400 MHz, CDCl3) δ 3.51-3.42 (m, 4 H), 3.25 (t, J=7.4 Hz, 2 H), 3.02 (t, J=6.0 Hz, 2 H), 2.20 (m, 2 H), 1.69 (m, 2 H).

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. filtrationfiltered
  3. concentrationThe filtrate was concentrated in vacuo
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated
  6. customchromatographed (0 to 5%, methanol in dichloromethane)

Sources & evidence

ORD record
ord-c9e3d2126e664214ba4741a0349b3446
Source dataset
uspto-grants-2014_04
Patent number
US08691991B2

Reaction notes

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