Hydrochloric Acid → HCID 18536114, compound

HRID 412188Notes

Reaction equation

HRID 412188 reaction equation
Cl.N[C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([O:13][S:14]([CH3:17])(=[O:16])=[O:15])[CH:11]=2)[C:6]([Br:18])=[CH:5][CH:4]=1.Cl.N([O-])=O.[Na+].[I-:24].[K+]>O.ClCCl>[Br:18][C:6]1[CH:5]=[CH:4][C:3]([I:24])=[C:12]2[C:7]=1[CH:8]=[CH:9][C:10]([O:13][S:14]([CH3:17])(=[O:16])=[O:15])=[CH:11]2

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 4875Potassium IodideHCID 18536127HCID 18536127, compoundHCID 23668193Sodium Nitrite

Product 1

HCID 18536114HCID 18536114, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolvent3×HCID 6344DichloromethaneSolvent

Procedure

To a solution of the product from Step D (1.50 g, 4.25 mmol) in 16 mL of 1:1THF/3M HCl solution at 0° C. was added NaNO2 as a 40 wt % solution in water (0.626 mL, 4.68 mmol). After 15 minutes, a solution of potassium iodide (2.12 g, 12.76 mmol) in 5 mL of water was added, and the solution was stirred for 3 hours. The reaction was poured into dichloromethane and water, the aqueous layer was extracted with dichloromethane, and the combined organic extracts were dried over Na2SO4, filtered, and concentrated in vacuo. The residue was purified by flash column chromatography on silica gel (20-30% EtOAc/hexane) to yield the desired product as a white solid.

Workup

  1. extractionthe aqueous layer was extracted with dichloromethane
  2. dry with materialthe combined organic extracts were dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by flash column chromatography on silica gel (20-30% EtOAc/hexane)

Sources & evidence

ORD record
ord-f3cb98823e8b425ca7d425706d01c167
Source dataset
uspto-grants-2003_05
Patent number
US06562823B1

Reaction notes

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