Isopropyl iodide → HCID 18509231, compound

HRID 1356663Notes

Reaction equation

HRID 1356663 reaction equation
[Na].[F:2][C:3]1[CH:19]=[CH:18][C:6]([NH:7][S:8]([C:11]2[CH:16]=[CH:15][C:14]([CH3:17])=[CH:13][CH:12]=2)(=[O:10])=[O:9])=[C:5]([N+:20]([O-:22])=[O:21])[CH:4]=1.[CH:23](I)([CH3:25])[CH3:24].[OH-].[Na+]>CN(C=O)C>[F:2][C:3]1[CH:19]=[CH:18][C:6]([N:7]([CH:23]([CH3:25])[CH3:24])[S:8]([C:11]2[CH:12]=[CH:13][C:14]([CH3:17])=[CH:15][CH:16]=2)(=[O:10])=[O:9])=[C:5]([N+:20]([O-:22])=[O:21])[CH:4]=1

Participants

5

Reactant 3

HCID 6362Isopropyl iodideHCID 14798Sodium HydroxideHCID 698223224'-Fluoro-2'-nitro-p-toluenesulfonanilide sodium salt

Product 1

HCID 18509231HCID 18509231, compoundYield 43.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4′-Fluoro-2′-nitro-p-toluenesulfonanilide sodium salt (66.46 g (200 mmol)) was dissolved in DMF (66 ml). To this, under heating in an oil bath kept at 120° C., isopropyl iodide (102.0 g (600 mmol)) was added over a period of 20 minutes. The resulting mixture was left to cool to room temperature, mixed with 1% aqueous sodium hydroxide solution and stirred. The resulting crystals were filtered, washed with water and ethanol, successively. The crude crystals thus obtained were recrystallized from ethyl acetate to give 30.58 g (43%) of the title compound as pale yellow crystals.

Workup

  1. temperatureTo this, under heating in an oil bath
  2. customkept at 120° C.
  3. waitThe resulting mixture was left
  4. filtrationThe resulting crystals were filtered
  5. washwashed with water and ethanol
  6. customThe crude crystals thus obtained
  7. customwere recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-245515be2ff242e5957a769cea9f5de7
Source dataset
uspto-grants-2003_07
Patent number
US06586617B1

Reaction notes

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