Triethylamine → S-[4-(benzenesulfonyloxy)phenyl] O-ethyl S-n-propyl phosphorodithioate

HRID 2083702Notes

Reaction equation

HRID 2083702 reaction equation
[P:1](=[O:10])(Cl)([S:5][CH2:6][CH2:7][CH3:8])[O:2][CH2:3][CH3:4].[C:11]1([S:17]([O:20][C:21]2[CH:26]=[CH:25][C:24]([SH:27])=[CH:23][CH:22]=2)(=[O:19])=[O:18])[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.C(N(CC)CC)C.P([S-])(=S)([O-])[O-]>C(#N)C>[P:1]([S:27][C:24]1[CH:23]=[CH:22][C:21]([O:20][S:17]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)(=[O:19])=[O:18])=[CH:26][CH:25]=1)(=[O:10])([S:5][CH2:6][CH2:7][CH3:8])[O:2][CH2:3][CH3:4]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 177047PhosphorodithioateHCID 11745722O-Ethyl S-propyl chlorothiophosphateHCID 203573644-(Benzenesulfonyloxy)thiophenol

Product 1

HCID 20357386S-[4-(benzenesulfonyloxy)phenyl] O-ethyl S-n-propyl phosphorodithioate

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent3×

Conditions

Temperature
4 °C

Procedure

A solution of 5.47 g. (0.026 mole) of O-ethyl S-n-propyl phosphorochloridothioate in 20 ml. of acetonitrile is charged in one portion to a solution of 6.65 g. (0.025 mole) of 4-(benzenesulfonyloxy)thiophenol in 200 ml. of acetonitrile. The solution is stirred and cooled to 4° C. while 2.53 g. (0.025 mole) of triethylamine in 20 ml. of acetonitrile is added dropwise over a 30 minute period. The mixture is held at 5° C. for an additional hour and then concentrated in vacuo. The residue, a mixture of oil and solid, is taken up in 200 ml. of benzene and filtered to remove amine hydrochloride. The filtrate is washed once with 50 ml. of 5% sodium bicarbonate, once with 30 ml. of water, once with 30 ml. of saturated sodium chloride, dried over sodium sulfate, and concentrated in vacuo to give 9.1 g. (84%) of the phosphorodithioate as a pale yellow oil. Anal. calc. (found): C 47.2 (47.3); H 4.8 (5.15).

Workup

  1. waitThe mixture is held at 5° C. for an additional hour
  2. concentrationconcentrated in vacuo
  3. additionThe residue, a mixture of oil and solid
  4. filtrationof benzene and filtered
  5. customto remove amine hydrochloride
  6. washThe filtrate is washed once with 50 ml
  7. dry with materialof saturated sodium chloride, dried over sodium sulfate
  8. concentrationconcentrated in vacuo
  9. customto give 9.1 g

Sources & evidence

ORD record
ord-f5b56e32c5a84cf2a4fb7ad26dfe752b
Source dataset
uspto-grants-1978_04
Patent number
US04086337

Reaction notes

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