Hydrochloric Acid → HCID 89656451, compound

HRID 633547Notes

Reaction equation

HRID 633547 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

A solution of the product from Example 51B (2.8 g, 9.32 mmol) in dioxane (20.0 mL) at 0° C. was treated with concentrated hydrogen chloride (40 mL, 9.32 mmol), stirred for 15 minutes and treated with a solution of sodium nitrite (0.772 g, 11.19 mmol) in water (10 mL). The mixture was stirred for 1 hour at 0° C., treated with a solution of potassium iodide (3.10 g, 18.65 mmol) in water (10 mL) and stirred for 1 hour at ambient temperature. The mixture was partitioned between ethyl acetate and water. The organic layer was washed with saturated sodium thiosulfate, water, saturated aqueous sodium chloride, dried (MgSO4), filtered, and concentrated. Purification by chromatography (silica gel, 0-60% ethyl acetate in hexane) afforded the title compound (2.24 g, 58%).

Workup

  1. stirringThe mixture was stirred for 1 hour at 0° C.
  2. stirringstirred for 1 hour at ambient temperature
  3. customThe mixture was partitioned between ethyl acetate and water
  4. washThe organic layer was washed with saturated sodium thiosulfate, water, saturated aqueous sodium chloride
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customPurification by chromatography (silica gel, 0-60% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-58f4df414ecd477aa5253566397afafa
Source dataset
uspto-grants-2016_04
Patent number
US09321764B2

Reaction notes

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