Ethanolamine → HCID 86761684, compound

HRID 1879614Notes

Reaction equation

HRID 1879614 reaction equation
FC(C(F)(F)F)(C(F)(F)F)C[CH:4]([CH2:12][C:13](F)([C:18](F)(F)F)[C:14]([F:17])([F:16])[F:15])[CH2:5][CH2:6][CH2:7][S:8](Cl)(=[O:10])=[O:9].[CH2:31]([CH2:33][NH2:34])[OH:32]>ClCCl>[OH:32][CH2:31][CH2:33][NH:34][S:8]([CH2:7][CH2:6][CH2:5][CH2:4][CH2:12][CH:13]([C:14]([F:15])([F:16])[F:17])[CH3:18])(=[O:9])=[O:10]

Participants

4

Reactant 2

HCID 700EthanolamineHCID 58901172HCID 58901172, compound

Product 1

HCID 86761684HCID 86761684, compoundYield 35.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

Referring to scheme (42) above, a solution of the 6,7,7,7-tetrafluoro-4-(2,3,3,3-tetrafluoro-2-trifluoromethyl-propyl)-6-trifluoromethyl heptane-1-sulfonyl chloride (25 grams), described above, in 125 mL dichloromethane can be added to a cooled solution (0° C.-5° C.) of ethanolamine (17.6 grams) in dichloromethane (125 mL) drop-wise to form a mixture. The mixture can be agitated, allowed to warm to room temperature, and diluted with dichloromethane (250 mL). The diluted mixture can be washed with deionized water (250 mL). 5% (wt/wt) HCl (250 mL), and saturated bicarbonate solution (250 mL). The organic layer can be separated, dried over sodium sulfate, filtered, and concentrated under vacuum to afford 6,7,7,7-tetrafluoro-4-(2,3,3,3-tetrafluoro-2-trifluoromethyl-propyl)-propyl)-6-trifluoromethyl-heptane-1-sulfonic acid (2-hydroxy-ethyl)-amide (5.0 grams) with residual dichloromethane and ethanolamine by NMR analysis.

Workup

  1. customto form a mixture
  2. washThe diluted mixture can be washed with deionized water (250 mL)
  3. customThe organic layer can be separated
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-484125d7d6184b3598e486f530447a3d
Source dataset
uspto-grants-2012_11
Patent number
US08318656B2

Reaction notes

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