2-(Perfluorohexyl)ethanesulfonyl chloride → HCID 53469612, compound

HRID 1026192Notes

Reaction equation

HRID 1026192 reaction equation
Cl.[Cl:2][CH2:3][CH2:4][CH2:5][NH2:6].[F:7][C:8]([F:31])([CH2:25][CH2:26][S:27](Cl)(=[O:29])=[O:28])[C:9]([F:24])([F:23])[C:10]([F:22])([F:21])[C:11]([F:20])([F:19])[C:12]([F:18])([F:17])[C:13]([F:16])([F:15])[F:14]>COCCOC>[C:13]([C:12]([C:11]([C:10]([C:9]([C:8]([CH2:25][CH2:26][S:27]([NH:6][CH2:5][CH2:4][CH2:3][Cl:2])(=[O:29])=[O:28])([F:7])[F:31])([F:24])[F:23])([F:22])[F:21])([F:20])[F:19])([F:18])[F:17])([F:16])([F:15])[F:14]

Participants

4

Reactant 2

HCID 1196852-(Perfluorohexyl)ethanesulfonyl chlorideHCID 114690951-Propanamine, 3-chloro-, hydrochloride

Product 1

HCID 53469612HCID 53469612, compound

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent2×

Procedure

3-chloropropylamine hydrochloride (6.0 g), diaza(1,3)bicyclo[5.4.0]-undecane (DBU, 4.1 g) and 1,2-dimethoxyethane (21.5 g) solvent were placed in the round bottom flask equipped with mechanical stirring under nitrogen. Solution of 2-(perfluorohexyl)ethanesulfonyl chloride CF3(CF2)5(CH2)2SO2Cl (10.1 g), in 1,2-dimethoxyethane (10 g) solvent was added dropwise during 30 minutes at 20-25° C. while stirring at 250 rpm. Then additional DBU (2.6 g) was added. Reaction mixture was stirred for 2 h after the DBU addition was completed. The reaction was monitored by GC to ensure the complete conversion of 2-(perfluorohexyl)ethanesulfonyl chloride. The final reaction mixture was filtered from solids through 2 mm layer of CELITE 545. The solids were washed with 1,2-dimethoxyethane and combined filtrate was evaporated in vacuum to obtain 11.3 g of crude CF3(CF2)5(CH2)2SO2NH(CH2)3Cl as yellow solid. 9.5 g of the crude product was additionally dissolved in hot toluene (7 g) and washed with 14 mL of 2.5 wt % HCl aqueous solution, followed with 12 mL water wash. Toluene solution was evaporated in vacuum to obtain 8.35 g of CF3(CF2)5(CH2)2SO2NH(CH2)3Cl (GC purity 93%, yield 88%).

Workup

  1. customequipped
  2. stirringwhile stirring at 250 rpm
  3. customReaction mixture
  4. stirringwas stirred for 2 h
  5. customThe final reaction mixture
  6. filtrationwas filtered from solids through 2 mm layer of CELITE 545
  7. washThe solids were washed with 1,2-dimethoxyethane
  8. customwas evaporated in vacuum

Sources & evidence

ORD record
ord-1936564014aa4fa9a9e70614849681ef
Source dataset
uspto-grants-2014_05
Patent number
US08729138B2

Reaction notes

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