Sodium Thiosulfate → HCID 23591426, compound

HRID 1919598Notes

Reaction equation

HRID 1919598 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([NH:11][C:12](=[O:14])[CH3:13])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].[I:15]Cl.[O-]S([O-])(=S)=O.[Na+].[Na+]>C(Cl)Cl.CC(O)=O>[I:15][C:6]1[CH:7]=[C:8]([O:9][CH3:10])[C:3]([O:2][CH3:1])=[CH:4][C:5]=1[NH:11][C:12](=[O:14])[CH3:13]

Participants

6

Reactant 3

HCID 24477Sodium ThiosulfateHCID 24640Iodine chlorideHCID 244160N-(3,4-Dimethoxyphenyl)acetamide

Product 1

HCID 23591426HCID 23591426, compoundYield 73%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of N-(3,4-dimethoxyphenyl)acetamide (6.3 g, 32.0 mmol) in DCM (100 mL) and AcOH (6.5 mL) was added a solution of iodine monochloride (6.3 g, 39 mmol) in DCM (50 mL) dropwise. The reaction mixture was stirred at r.t. for 16 h. Aqueous sat. Na2S2O3 (500 mL) was added. The organic fraction was separated, washed with water (2×250 mL), then brine (100 mL), dried (Na2SO4), filtered and concentrated in vacuo. Purification by column chromatography (SiO2, 50% EtOAc/hexanes) gave the title compound (7.5 g, 72%) as a dark solid. LCMS (ES+) 321.8 (M+H)+, RT 2.67 minutes (Method 4).

Workup

  1. customThe organic fraction was separated
  2. washwashed with water (2×250 mL)
  3. dry with materialbrine (100 mL), dried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customPurification by column chromatography (SiO2, 50% EtOAc/hexanes)

Sources & evidence

ORD record
ord-06cd6359e89045549535831c841775a3
Source dataset
uspto-grants-2012_05
Patent number
US08168634B2

Reaction notes

Loading…