1,4-Dioxane → HCID 67468620, compound

HRID 1845910Notes

Reaction equation

HRID 1845910 reaction equation
[CH3:1][S:2][C:3]1[S:4][C:5]2[CH:11]=[C:10]([NH2:12])[CH:9]=[CH:8][C:6]=2[N:7]=1.O1CCOCC1.C1C=C[NH+]=CC=1.[Br:25][Br-]Br>CCOC(C)=O>[Br:25][C:11]1[C:5]2[S:4][C:3]([S:2][CH3:1])=[N:7][C:6]=2[CH:8]=[CH:9][C:10]=1[NH2:12]

Participants

4

Reactant 2

HCID 312751,4-DioxaneHCID 2741512-(methylthio)-1,3-benzothiazol-6-amine

Product 1

HCID 67468620HCID 67468620, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a round bottom flask was added 2-(methylthio)-1,3-benzothiazol-6-amine (0.301 g, 1.533 mmol), Dioxane (10 mL), and pyridinium bromide perbromide (0.589 g, 1.840 mmol). The reaction mixture was then stirred at room temperature for ˜5 minutes, then suspended in EtOAc, washed with sat'd Na2S2O3, then with sat'd NaHCO3, then water, then brine. Organics were then dried over Na2SO4 filtered & concentrated. The resulting residue was purified using silica gel chromatography (0-45% ethyl acetate/hexanes) to give 7-bromo-2-(methylthio)-1,3-benzothiazol-6-amine (13-1) as a tan solid. HRMS (M+H)+: observed=274.9307, calculated=274.9307.

Workup

  1. washwashed with sat'd Na2S2O3
  2. dry with materialOrganics were then dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe resulting residue was purified

Sources & evidence

ORD record
ord-92e2691873ed4117806203afd1b9e45e
Source dataset
uspto-grants-2015_02
Patent number
US08952005B2

Reaction notes

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