Potassium Iodide → HCID 66901532, compound

HRID 1692382Notes

Reaction equation

HRID 1692382 reaction equation
N([O-])=O.[Na+].[CH3:5][O:6][C:7]1[CH:8]=[C:9]([C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([C:21]([F:24])([F:23])[F:22])[CH:16]=2)[CH:10]=[C:11]([CH3:14])[C:12]=1N.[I-:25].[K+]>O.Cl>[I:25][C:12]1[C:11]([CH3:14])=[CH:10][C:9]([C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([C:21]([F:24])([F:23])[F:22])[CH:16]=2)=[CH:8][C:7]=1[O:6][CH3:5]

Participants

6

Reactant 3

HCID 4875Potassium IodideHCID 23668193Sodium NitriteHCID 66901621HCID 66901621, compound

Product 1

HCID 66901532HCID 66901532, compoundYield 49%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 962WaterSolvent3×

Procedure

A solution of 3.10 g (45.0 mmol) of sodium nitrite in 20 ml of H2O was added to a suspension of 11.50 g (40.90 mmol) of 3-methoxy-5-methyl-3′-trifluoromethyl-biphenyl-4-ylamine in 35.0 ml of HCl (25%) and 190 ml of H2O at 2° C.; after 30 min, the light-brown solution formed was added at 0° C. to a solution of 6.95 g (433.4 mmol) of potassium iodide in 40 ml of H2O and the reaction mixture was warmed up to RT. 4 hours later, it was poured then into crashed ice and extracted twice with EtOAc; the organic phases were washed with sodium bicarbonate solution and with water, dried over magnesium sulfate, filtered and evaporated. The residue was purified by flash column chromatography (heptane/EtOAc 1:0 to 4:1) to give 7.79 g (49%) of the title compound as yellow oil. MS: 392.0 (M+).

Workup

  1. customthe light-brown solution formed
  2. addition4 hours later, it was poured
  3. extractionextracted twice with EtOAc
  4. washthe organic phases were washed with sodium bicarbonate solution and with water
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. customevaporated
  8. customThe residue was purified by flash column chromatography (heptane/EtOAc 1:0 to 4:1)

Sources & evidence

ORD record
ord-bc8ddcffddb64d8faeb6b327dce37cb3
Source dataset
uspto-grants-2012_04
Patent number
US08153805B2

Reaction notes

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