Sodium Thiosulfate → HCID 21771543, compound

HRID 2189256Notes

Reaction equation

HRID 2189256 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([CH2:10][NH:11][C:12](=[O:14])[CH3:13])=[CH:9][C:4]=2[O:3][CH2:2]1.[I:15]Cl.[O-]S([O-])(=S)=O.[Na+].[Na+]>C(Cl)Cl>[I:15][C:7]1[C:8]([CH2:10][NH:11][C:12](=[O:14])[CH3:13])=[CH:9][C:4]2[O:3][CH2:2][O:1][C:5]=2[CH:6]=1

Participants

5

Reactant 3

HCID 24477Sodium ThiosulfateHCID 24640Iodine chlorideHCID 290549N-[(2H-1,3-Benzodioxol-5-yl)methyl]ethanimidic acid

Product 1

HCID 21771543HCID 21771543, compoundYield 38%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

N-(benzo[d][1,3]dioxol-5-ylmethyl)acetamide (9.24 g, 47.9 mmol) was added to 1.0 M solution of iodine monochloride in methylene chloride (80 mL). The mixture was stirred at room temperature for 2 hours, and then the mixture was poured into 10% Na2S2O3 and stirred until the red color faded. It was then extracted with CH2Cl2 and the organic layer was washed with water and brine, dried and concentrated to get the crude product which was purified by column chromatography (mobile phase: petroleum/methylene chloride=1/19) to give N-((6-iodobenzo[d][1,3]dioxol-5-yl)methyl)acetamide compound as a white solid (5.82 g, 38%). LC-MS: 320 [M+1]+. 1H-NMR (DMSO-d6): δ 1.89 (s, 3H), 4.11 (d, 2H, J=6.0 Hz), 6.04 (s, 2H), 7.07 (s, 1H), 7.37 (s, 1H), 8.28 (t, 1H, J=6.0 Hz).

Workup

  1. stirringstirred until the red color
  2. extractionIt was then extracted with CH2Cl2
  3. washthe organic layer was washed with water and brine
  4. customdried
  5. concentrationconcentrated
  6. customto get the crude product which
  7. customwas purified by column chromatography (mobile phase: petroleum/methylene chloride=1/19)

Sources & evidence

ORD record
ord-89dcc2b3632a41ada4141a5bd212d9fb
Source dataset
uspto-grants-2012_12
Patent number
US08324240B2

Reaction notes

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