Sodium Thiosulfate → HCID 57929922, compound

HRID 1930068Notes

Reaction equation

HRID 1930068 reaction equation
[I:1]Cl.C[O:4]/[N:5]=[C:6](/[C:10]1[CH:15]=[CH:14][C:13]([F:16])=[CH:12][C:11]=1[F:17])\[C:7]#[C:8][CH3:9].S([O-])([O-])(=O)=S.[Na+].[Na+]>C(Cl)Cl>[F:17][C:11]1[CH:12]=[C:13]([F:16])[CH:14]=[CH:15][C:10]=1[C:6]1[C:7]([I:1])=[C:8]([CH3:9])[O:4][N:5]=1

Participants

5

Reactant 3

HCID 24477Sodium ThiosulfateHCID 24640Iodine chlorideHCID 57929916HCID 57929916, compound

Product 1

HCID 57929922HCID 57929922, compoundYield 47%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Iodine monochloride (2.13 g, 13.1 mmol) was dissolved in DCM (15 mL) then the solution was added over about 10 min to the (E)-1-(2,4-difluorophenyl)but-2-yn-1-one O-methyl oxime (2.29 g, 10.9 mmol) in DCM (100 mL). The mixture was stirred for about 1 h then saturated aqueous sodium thiosulfate (50 mL) was added. The mixture was stirred for about 10 min then the layers were separated. The aqueous layer was extracted with DCM (25 mL) then the combined organics were dried over MgSO4, filtered and concentrated under reduced pressure. The material was purified by flash chromatography on silica gel with heptane/EtOAc (95:5) as an eluent to give the title compound (1.64 g, 47%): LC/MS (Table 1, Method g) Rt=2.65 min; MS m/z: 322.0 (M+H)+.

Workup

  1. stirringThe mixture was stirred for about 10 min
  2. customthe layers were separated
  3. extractionThe aqueous layer was extracted with DCM (25 mL)
  4. dry with materialthe combined organics were dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe material was purified by flash chromatography on silica gel with heptane/EtOAc (95:5) as an eluent

Sources & evidence

ORD record
ord-d04852803c8b40b59c2232b4e23c874c
Source dataset
uspto-grants-2012_05
Patent number
US08188083B2

Reaction notes

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