Acetonitrile → 4-(Heptafluoropropylthio)aniline

HRID 1696953Notes

Reaction equation

HRID 1696953 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 20 ml of an acetonitrile solution of 1.25 g of 4-aminothiophenol and 1.11 g of triethylamine was added 5.91 g of 1-iodoheptafluoro-n-propane. The resulting mixture was stirred at room temperature for 3 hours, diluted with ether, and then washed with aqueous 1N sodium hydroxide solution, purified by silica gel column chromatography using an eluent (development solvent; hexane:ethyl acetate=4:1) to obtain 1.85 g of the desired product (Yield: 63%).

Workup

  1. washwashed with aqueous 1N sodium hydroxide solution
  2. custompurified by silica gel column chromatography

Sources & evidence

ORD record
ord-54274d3c1c6e4dd8a3b2e584862bc5bf
Source dataset
uspto-grants-2012_04
Patent number
US08163804B2

Reaction notes

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