Sodium Thiosulfate → N-(6-Iodo-2H-1,3-benzodioxol-5-yl)acetamide

HRID 1919597Notes

Reaction equation

HRID 1919597 reaction equation
[CH2:1]1[O:13][C:12]2[CH:11]=[CH:10][C:5]([NH:6][C:7](=[O:9])[CH3:8])=[CH:4][C:3]=2[O:2]1.[I:14]Cl.[O-]S([O-])(=S)=O.[Na+].[Na+]>C(Cl)Cl.CC(O)=O>[I:14][C:10]1[C:5]([NH:6][C:7](=[O:9])[CH3:8])=[CH:4][C:3]2[O:2][CH2:1][O:13][C:12]=2[CH:11]=1

Participants

6

Reactant 3

HCID 24477Sodium ThiosulfateHCID 24640Iodine chlorideHCID 98688N-(2H-1,3-Benzodioxol-5-yl)acetamide

Product 1

HCID 53488067N-(6-Iodo-2H-1,3-benzodioxol-5-yl)acetamideYield 63.4%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a stirred solution of 3′,4′-methylenedioxyacetanilide (7.7 g, 43.0 mmol) in DCM (100 mL) and AcOH (6.5 mL) was added a solution of iodine monochloride (6.3 g, 38.8 mmol) in DCM (50 mL). The reaction mixture was stirred at r.t. for 16 h. Aqueous sat. Na2S2O3 (500 mL) was added. The organic fraction was separated, dried (Na2SO4), filtered and concentrated in vacuo. Purification by column chromatography (SiO2, 50% EtOAc/hexanes) gave the title compound (7.5 g, 57%) as a brown solid. LCMS (ES+) 306.0 (M+H)+, RT 2.75 minutes (Method 4).

Workup

  1. customThe organic fraction was separated
  2. dry with materialdried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customPurification by column chromatography (SiO2, 50% EtOAc/hexanes)

Sources & evidence

ORD record
ord-7ffdbb604b5946dca6dde8164ccb6c3f
Source dataset
uspto-grants-2012_05
Patent number
US08168634B2

Reaction notes

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