Hydrochloric Acid → HCID 89656451, compound

HRID 930891Notes

Reaction equation

HRID 930891 reaction equation
N[C:2]1[CH:3]=[C:4]([S:17]([NH2:20])(=[O:19])=[O:18])[CH:5]=[CH:6][C:7]=1[O:8][C:9]1[CH:14]=[CH:13][C:12]([F:15])=[CH:11][C:10]=1[F:16].Cl.N([O-])=O.[Na+].[I-:26].[K+]>O1CCOCC1.O>[F:16][C:10]1[CH:11]=[C:12]([F:15])[CH:13]=[CH:14][C:9]=1[O:8][C:7]1[CH:6]=[CH:5][C:4]([S:17]([NH2:20])(=[O:19])=[O:18])=[CH:3][C:2]=1[I:26]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 4875Potassium IodideHCID 23668193Sodium NitriteHCID 89656036HCID 89656036, compound

Product 1

HCID 89656451HCID 89656451, compoundYield 58.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 312751,4-DioxaneSolvent

Procedure

To a solution of Example 146b (2.8 g, 9.32 mmol) in dioxane (20 mL) at 0° C. was added concentrated hydrochloric acid (40 mL, 9.32 mmol). The mixture was stirred 15 minutes and a solution of sodium nitrite (0.772 g, 11.19 mmol) in water (10 mL) was added. The mixture was stirred for 1 hour at 0° C. A solution of potassium iodide (3.10 g, 18.7 mmol) in water (10 mL) was added and stirring was continued 1 hour at ambient temperature. The mixture was partitioned between ethyl acetate and water. The organic layer was washed with saturated sodium thiosulfate, water, and saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate, filtered, and concentrated. The residue was purified by flash column chromatography (silica gel, 0-60% ethyl acetate in hexane) to provide the title compound (2.24 g, 58.4% yield).

Workup

  1. stirringThe mixture was stirred for 1 hour at 0° C
  2. stirringstirring
  3. waitwas continued 1 hour at ambient temperature
  4. customThe mixture was partitioned between ethyl acetate and water
  5. washThe organic layer was washed with saturated sodium thiosulfate, water, and saturated aqueous sodium chloride
  6. dry with materialdried over anhydrous magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe residue was purified by flash column chromatography (silica gel, 0-60% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-fabc4f815a3347ae86df4fa262dd4eae
Source dataset
uspto-grants-2016_03
Patent number
US09296741B2

Reaction notes

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