Triethylamine → HCID 53469612, compound

HRID 1625182Notes

Reaction equation

HRID 1625182 reaction equation
[C:1]([C:5]([C:8]([C:11]([C:14]([C:17]([CH2:20][CH2:21][S:22](Cl)(=[O:24])=[O:23])([F:19])[F:18])([F:16])[F:15])([F:13])[F:12])([F:10])[F:9])([F:7])[F:6])([F:4])([F:3])[F:2].Cl.[Cl:27][CH2:28][CH2:29][CH2:30][NH2:31].C(N(CC)CC)C>COCCOC>[C:1]([C:5]([C:8]([C:11]([C:14]([C:17]([CH2:20][CH2:21][S:22]([NH:31][CH2:30][CH2:29][CH2:28][Cl:27])(=[O:24])=[O:23])([F:19])[F:18])([F:16])[F:15])([F:13])[F:12])([F:10])[F:9])([F:7])[F:6])([F:4])([F:3])[F:2]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 1196852-(Perfluorohexyl)ethanesulfonyl chlorideHCID 114690951-Propanamine, 3-chloro-, hydrochloride

Product 1

HCID 53469612HCID 53469612, compoundYield 97.5%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent2×

Procedure

CF3(CF2)5(CH2)2SO2Cl (10 g), 3-chloropropyl amine hydrochloride (4.1 g), and 1,2-dimethoxyethane (20 g) solvent were added to the round bottom flask equipped with mechanical stirring under nitrogen. Solution of triethylamine (4.5 g) in 1,2-dimethoxyethane (10 g) solvent was added dropwise during 30 min at 20-30° C. at 250 rpm. Stirred for 12 h after the addition is completed. The reaction was monitored by GC to ensure the complete conversion 1. The final reaction mixture with pH of about 5 was filtered from solids through 2 mm layer of CELITE 545. The solids were washed with 1,2-dimethoxyethane (7 g) and combined filtrate was evaporated in vacuum to obtain 11.0 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 to remove traces of NH2(CH2)3Cl.

Workup

  1. customequipped
  2. stirringStirred for 12 h
  3. additionafter the addition
  4. customThe final reaction mixture with pH of about 5
  5. filtrationwas filtered from solids through 2 mm layer of CELITE 545
  6. washThe solids were washed with 1,2-dimethoxyethane (7 g)
  7. customwas evaporated in vacuum

Sources & evidence

ORD record
ord-4194c6cee1fd4133a2e4405d7f5de18b
Source dataset
uspto-grants-2014_07
Patent number
US08779196B2

Reaction notes

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