Sodium Iodide → 2,3-Dihydro-1,4-benzothiazine

HRID 424586Notes

Reaction equation

HRID 424586 reaction equation
Cl[CH2:2][CH2:3][S:4][C:5]1[CH:11]=[CH:10][CH:9]=[CH:8][C:6]=1[NH2:7].C(=O)([O-])[O-].[K+].[K+].[I-].[Na+]>CN(C=O)C.C(OCC)(=O)C>[S:4]1[CH2:3][CH2:2][NH:7][C:6]2[CH:8]=[CH:9][CH:10]=[CH:11][C:5]1=2

Participants

6

Reactant 3

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 12761371HCID 12761371, compound

Product 1

HCID 1510642,3-Dihydro-1,4-benzothiazineYield 99%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
90 °C

Procedure

To a stirred solution of 2-(2-chloroethylthio)aniline (850 mg, 4.53 mmol) in DMF (10 mL) was added potassium carbonate (1878 mg, 13.59 mmol) followed by sodium iodide (67.9 mg, 0.453 mmol). The resulting mixture was heated to 90° C. and stirred overnight. The reaction mixture was then cooled to room temperature, diluted with ethyl acetate, and washed with water (3×) and brine. The organic phase was dried, filtered, concentrated, and then chromatographed in 9:1 hexanes:ethyl acetate, giving an orange oil (675 mg, 99%). 1H NMR (DMSO-d6) δ 6.85-6.75 (m, 2H), 6.51-6.39 (m, 2H), 6.00 (brs, 1H), 3.49-3.44 (m, 2H), 2.98-2.93 (m, 2H); ESI-MS (m/z, %): 152 (MH+, 100), 124 (44).

Workup

  1. temperatureThe reaction mixture was then cooled to room temperature
  2. washwashed with water (3×) and brine
  3. customThe organic phase was dried
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customchromatographed in 9:1 hexanes

Sources & evidence

ORD record
ord-149cb4f121e84d469e927e3479021c6a
Source dataset
uspto-grants-2012_01
Patent number
US08106043B2

Reaction notes

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