Acetonitrile → 4-(Heptafluoropropylthio)aniline

HRID 511760

Reaction equation

HRID 511760 reaction equation
C(#N)C.[NH2:4][C:5]1[CH:10]=[CH:9][C:8]([SH:11])=[CH:7][CH:6]=1.C(N(CC)CC)C.I[C:20]([F:29])([F:28])[C:21]([F:27])([F:26])[C:22]([F:25])([F:24])[F:23]>CCOCC>[F:26][C:21]([F:27])([C:22]([F:25])([F:24])[F:23])[C:20]([F:29])([F:28])[S:11][C:8]1[CH:9]=[CH:10][C:5]([NH2:4])=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 6342AcetonitrileHCID 8471TriethylamineHCID 145104-AminothiophenolHCID 33977Perfluoropropyl iodide

Product 1

HCID 20526094-(Heptafluoropropylthio)anilineYield 63.2%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To an acetonitrile solution (20 ml) of 4-aminothiophenol (1.25 g, 9.98 mmol) and triethylamine (1.11 g, 11.0 mmol) was added 1-iodoheptafluoro-n-propane (5.91 g, 19.9 mmol), and the resultant mixture was stirred at room temperature for 3 hours. The mixture was diluted with ether, and washed with a 1N sodium hydroxide aqueous solution. Then, the product was purified by silica gel column chromatography (eluent; hexane:ethyl acetate=4:1) to obtain 1.85 g (yield 63%) of the title compound.

Workup

  1. washwashed with a 1N sodium hydroxide aqueous solution
  2. customThen, the product was purified by silica gel column chromatography (eluent; hexane:ethyl acetate=4:1)

Sources & evidence

ORD record
ord-832718530f554600bd472156ffa9057a
Source dataset
uspto-grants-2015_08
Patent number
US09101135B2

Linked notes

Loading…