Potassium Iodide → HCID 28480274, compound

HRID 1487079Notes

Reaction equation

HRID 1487079 reaction equation
[CH2:1]([C:3]1[CH:9]=[CH:8][CH:7]=[CH:6][C:4]=1[NH2:5])[CH3:2].[CH3:10][CH:11]([CH3:14])[CH2:12]O.[I-].[K+]>O.ClCCl>[CH2:1]([C:3]1[CH:9]=[CH:8][CH:7]=[CH:6][C:4]=1[NH:5][CH2:10][CH:11]([CH3:14])[CH3:12])[CH3:2]

Participants

6

Reactant 3

HCID 4875Potassium IodideHCID 6560IsobutanolHCID 113572-Ethylaniline

Product 1

HCID 28480274HCID 28480274, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6344DichloromethaneSolvent

Conditions

Temperature
150 °C

Procedure

2-ethylaniline (0.102 mL, 0.825 mmol), 2-methylpropan-1-ol (0.305 mL, 3.30 mmol), potassium iodide (274 mg, 1.650 mmol) and [Cp*IrCl2]2 (10.52 mg, 0.013 mmol) were added to a microwave vial with water (1.5 mL). This was heated, by microwaves, for 90 minutes at 150° C. Dichloromethane (10 mL) and water (10 mL) were added and the phases separated using a hydrophobic frit. The aqueous layer was further extracted with dichloromethane (15 mL). The combined organic layers were concentrated under vacuum and purified by silica (Si) chromatography (0-50% dichloromethane-cyclohexane gradient). The relevant fractions were concentrated to provide the product as a clear oil, 0.83 mg. LCMS [LCMS1] Rt 1.26 min, m/z (ES+) 178 (M+H).

Workup

  1. customthe phases separated
  2. extractionThe aqueous layer was further extracted with dichloromethane (15 mL)
  3. concentrationThe combined organic layers were concentrated under vacuum
  4. custompurified by silica (Si) chromatography (0-50% dichloromethane-cyclohexane gradient)
  5. concentrationThe relevant fractions were concentrated

Sources & evidence

ORD record
ord-64a6591a7c3041659fcdce46e957df41
Source dataset
uspto-grants-2016_08
Patent number
US09428452B2

Reaction notes

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