Potassium Iodide → HCID 18789864, compound

HRID 1106886Notes

Reaction equation

HRID 1106886 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:11][CH2:12][NH:13][CH:14]([CH3:16])[CH3:15])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].[N+:17]([C:20]1[CH:29]=[CH:28][C:23]([O:24][CH2:25][CH2:26]Br)=[C:22]([N:30]2[CH:34]=[CH:33][CH:32]=[CH:31]2)[CH:21]=1)([O-:19])=[O:18].[I-].[K+].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[N+:17]([C:20]1[CH:29]=[CH:28][C:23]([O:24][CH2:25][CH2:26][N:13]([CH2:12][CH2:11][C:5]2[CH:6]=[CH:7][C:8]([O:9][CH3:10])=[C:3]([O:2][CH3:1])[CH:4]=2)[CH:14]([CH3:16])[CH3:15])=[C:22]([N:30]2[CH:34]=[CH:33][CH:32]=[CH:31]2)[CH:21]=1)([O-:19])=[O:18]

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 1263584HCID 1263584, compoundHCID 18789849HCID 18789849, compound

Product 1

HCID 18789864HCID 18789864, compoundYield 19.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
85 °C

Procedure

2-(3,4-Dimethoxyphenyl)-N-isopropylethylamine (2.4 g, 11 mmol) and 1-[4-nitro-2-(1H-pyrrol-1-yl)phenoxy]-2-bromoethane (3.04 g, 10 mmol) were dissolved in DMF and, thereafter, potassium iodide (1.61 g, 11 mmol) and anhydrous potassium carbonate (1.5 g, 10 mmol) were added and the mixture was stirred at 80-90° C. for 1 h; thereafter, ice water was added and extraction was conducted with ethyl acetate. The extracted organic layer was dried with magnesium sulfate and the solvent was evaporated; the resulting residue was purified by being subjected to column chromatography on silica gel using a 7:3:1 solvent system of cyclohexane, ethyl acetate and methanol as an eluent. The fractions containing the product were collected and the solvent was evaporated to yield the end compound 1-[4-nitro-2-(1H-pyrrol-1-yl)phenoxy]-2-[N-(3,4-dimethoxyphenethyl)-N-isopropylamino]ethane (0.9 g).

Workup

  1. extractionextraction
  2. dry with materialThe extracted organic layer was dried with magnesium sulfate
  3. customthe solvent was evaporated
  4. customthe resulting residue was purified
  5. additionThe fractions containing the product
  6. customwere collected
  7. customthe solvent was evaporated

Sources & evidence

ORD record
ord-0b9d93b3d1204a25a59c68885aeee697
Source dataset
uspto-grants-2000_05
Patent number
US06057358

Reaction notes

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