Potassium Carbonate → HCID 53469612, compound

HRID 1026191Notes

Reaction equation

HRID 1026191 reaction equation
Cl.[Cl:2][CH2:3][CH2:4][CH2:5][NH2:6].C([O-])([O-])=O.[K+].[K+].[C:13]([C:17]([C:20]([C:23]([C:26]([C:29]([CH2:32][CH2:33][S:34](Cl)(=[O:36])=[O:35])([F:31])[F:30])([F:28])[F:27])([F:25])[F:24])([F:22])[F:21])([F:19])[F:18])([F:16])([F:15])[F:14]>COCCOC>[C:13]([C:17]([C:20]([C:23]([C:26]([C:29]([CH2:32][CH2:33][S:34]([NH:6][CH2:5][CH2:4][CH2:3][Cl:2])(=[O:36])=[O:35])([F:30])[F:31])([F:28])[F:27])([F:25])[F:24])([F:22])[F:21])([F:19])[F:18])([F:16])([F:15])[F:14]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 1196852-(Perfluorohexyl)ethanesulfonyl chlorideHCID 114690951-Propanamine, 3-chloro-, hydrochloride

Product 1

HCID 53469612HCID 53469612, compound

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent2×

Conditions

Temperature
75 °C

Procedure

3-chloropropyl amine hydrochloride (4.7 g), K2CO3 (6.9 g) and 1,2-dimethoxyethane (19.3 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 1 hour at room temperature while stirring at 250 rpm. After the addition was completed, the reaction was gradually heated to 75° C. and reacted for 12 h. The reaction was monitored by GC to ensure the complete conversion of CF3(CF2)5(CH2)2SO2Cl. The final reaction mixture with pH=3.5 was cooled down and filtered from solids through 2 mm layer of CELITE 545. The solids were washed with 1,2-dimethoxyethane (10 mL) and combined filtrate was evaporated in vacuum to obtain 8.2 g of CF3(CF2)5(CH2)2SO2NH(CH2)3Cl. The product was additionally dissolved in hot toluene (8 g) and washed with 15.5 mL of 1 wt % HCl aqueous solution.

Workup

  1. customequipped
  2. stirringwhile stirring at 250 rpm
  3. additionAfter the addition
  4. customreacted for 12 h
  5. customThe final reaction mixture with pH=3.5
  6. temperaturewas cooled down
  7. filtrationfiltered from solids through 2 mm layer of CELITE 545
  8. washThe solids were washed with 1,2-dimethoxyethane (10 mL)
  9. customwas evaporated in vacuum

Sources & evidence

ORD record
ord-984c8077d6e04010a0958efffbe36677
Source dataset
uspto-grants-2014_05
Patent number
US08729138B2

Reaction notes

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