Ethylamine → HCID 57160369, compound

HRID 373481Notes

Reaction equation

HRID 373481 reaction equation
[P:1](Cl)(Cl)([S:3][CH2:4][CH2:5][CH3:6])=[O:2].C([N:11]([CH2:14][CH3:15])CC)C.[F:16][C:17]1([F:27])[C:21]([F:23])([F:22])[C:20]([F:25])([F:24])[CH2:19][CH:18]1[OH:26].C(N)C>CCCCCC.C(Cl)Cl>[CH2:14]([NH:11][P:1](=[O:2])([S:3][CH2:4][CH2:5][CH3:6])[O:26][CH:18]1[CH2:19][C:20]([F:24])([F:25])[C:21]([F:22])([F:23])[C:17]1([F:27])[F:16])[CH3:15]

Participants

7

Reactant 4

HCID 6341EthylamineHCID 8471TriethylamineHCID 12941235S-Propyl phosphorodichloridothioateHCID 198104852,2,3,3,4,4-Hexafluorocyclopentanol

Product 1

HCID 57160369HCID 57160369, compoundYield 47.3%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8058HexaneSolvent

Conditions

Temperature
20 °C

Procedure

10 g (0.05 mol) of S-propyl dichlorothiophosphate are dissolved in 500 ml of hexane and to the solution there are first added, between 0° and -5° C., 10 ml (0.07 mol) of triethylamine, and then 10 g (0.052 mol) of 2,2,3,3,4,4-hexafluorocyclopentan-1-ol, dissolved in 25 ml of methylene chloride. The mixture is stirred for 2 hours at 20° C. and 5 g (0.11 mol) of ethylamine are then added dropwise to the reaction mixture at 20° C. To complete the reaction, the mixture is stirred for 24 hours at 20° C., the solid is filtered off, and the solvent is distilled off under reduced pressure. The residue is then purified further by filtration through silica gel (cyclohexane:ethyl acetate=7:3 parts by volume). After the solvent has been distilled off, 8.5 g (47% of theory) of O-(2,2,3,3,4,4-hexafluorocyclopentyl) S-propyl N-ethylthiophosphoramidate of refractive index nD20 =1.4292 are obtained.

Workup

  1. additionare first added, between 0° and -5° C.
  2. customthe reaction
  3. stirringthe mixture is stirred for 24 hours at 20° C.
  4. filtrationthe solid is filtered off
  5. distillationthe solvent is distilled off under reduced pressure
  6. filtrationThe residue is then purified further by filtration through silica gel (cyclohexane:ethyl acetate=7:3 parts by volume)
  7. distillationAfter the solvent has been distilled off

Sources & evidence

ORD record
ord-99f11e4d35894ee385e99c91620770c6
Source dataset
uspto-grants-1992_11
Patent number
US05164383

Reaction notes

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